bluuebunny/crossref_metadata_2025 huggingface dataset:
Construction of Alkylated Stereocenters
Authors: Seibel Zara M. , Lambert Tristan H.
Published: November 2020

Hirohisa Ohmiya and Masaya Sawamura at Hokkaido University reported (Angew. Chem. Int. Ed. 2013, 52, 5350) the copper-catalyzed, γ-selective allylation of terminal alkyne 1 to produce the chiral skipped enyne 3 with high ee. A method to synthe­size asymmetric skipped diene 6 via copper-catalyzed allylic allylation of diene 4 was developed (Chem. Commun. 2013, 49, 3309) by Ben L. Feringa at the University of Groningen. Prof. Feringa also disclosed (J. Am. Chem. Soc. 2013, 135, 2140) the regi­oselective and enantioselective allyl–allyl coupling of bromide 7 with allyl Grignard under Cu catalysis in the presence of phosphoramidite 8. James P. Morken of Boston College reported (Org. Lett. 2013, 15, 1432) the cross-coupling of allylboronate 11 with a mixture of alkenes 10a,b under palladium catalysis to produce diene 13 with high ee. Jian Liao at the Chengdu Institute of Biology Chinese Academy of Sciences and the University of Chinese Academy of Sciences reported (Angew. Chem. Int. Ed. 2013, 52, 4207) the palladium-catalyzed allylic alkylation of indole using the chi­ral bis(sulfoxide) phosphine ligand 15. Yi-Xia Jia at the Zhejiang University of Technology reported (J. Am. Chem. Soc. 2013, 135, 2983) the enantioselective alkyl­ation of indole to produce the trifluoromethyl adduct 19 using nickel catalysis in the presence of bisoxazoline ligand 18. Sarah E. Reisman at the California Institute of Technology disclosed (J. Am. Chem. Soc. 2013, 135, 7442) the reductive cross-coupling of acid chloride 20 and benzyl chloride 21 using a nickel complex with bisoxazoline ligand 22 and manganese(0) as reductant. Ilan Marek at the Technion-Israel Institute of Technology reported (Angew. Chem. Int. Ed. 2013, 52, 5333) a method for the construction of all-carbon quaternary stereocenters, such as the one present in aldehyde 25, using a diastereoselective car­bometallation of cyclopropene 24 followed by oxidation and ring opening. Switching from methyl Grignard and copper iodide to MeCuCNLi reverses the diastereoselec­tivity of the carbometallation and allows access to the opposite enantiomer. Matthew S. Sigman at the University of Utah reported (J. Am. Chem. Soc. 2013, 135, 6830) the redox–relay oxidative Heck arylation of alkenyl alcohol 27 with boronic acid 26 using a palladium catalyst and pyridine oxazole ligand 28 to produce the γ-substituted aldehyde 29.
Arrays of Stereogenic Centers: The Thomson Synthesis of (−)-Galactin
Authors: Taber Douglass F.
Published: November 2020

Hisashi Yamamoto of the University of Chicago and Chubu University developed (J. Am. Chem. Soc. 2014, 136, 1222) a tungsten catalyst for the enantioselective oxida­tion of allylic alcohols such as 1 to the epoxide 2. Homoallylic alcohols also worked well. Naoya Kumagai and Masakatsu Shibasaki of the Institute of Microbial Chemistry devised (Chem. Eur. J. 2014, 20, 68) a scalable Zn-catalyzed protocol for the coupling of 3 with 4 to give 5. Professor Shibasaki and Takumi Watanabe, also of the Institute of Microbial Chemistry, established (Org. Lett. 2014, 16, 3364) a Nb catalyst for the preparation of 8 by the Henry addition of 7 to 6. Wenhao Hu of East China Normal University effected (Synthesis 2014, 46, 1348) the coupling of 9 and 10 with two equivalents of aniline to give the diamine 10. Sanzhong Luo of the Institute of Chemistry, Beijing showed (Angew. Chem. Int. Ed. 2014, 53, 4149) that the adduct between 11 and an in situ formed N-nitroso could be reduced with high diastereoselectivity, leading to 12. Kumagai and Shibasaki also described (Angew. Chem. Int. Ed. 2014, 53, 5327) the assembly of 15 by the enantiose­lective addition 14 to 13. Bernhard Breit of the Albert-Ludwigs-Universität Freiburg effected (Synthesis 2014, 46, 1311) the carbonylation of the alkene 16 to give an alde­hyde that underwent in situ condensation with the imine 17, leading, after a subse­quent addition of vinyl magnesium chloride, to the lactone 18. Michael J. Krische of the University of Texas prepared (J. Am. Chem. Soc. 2014, 136, 8911) the diol 21 by adding the racemic epoxide 20 to the aldehyde 19. Martin Hiersemann of the Technische Universität Dortmund achieved (J. Org. Chem. 2014, 79, 3040) high enantioselectivity in the rearrangement of the enol ether 22 to 23. Michael T. Crimmins also observed (Org. Lett. 2014, 16, 2458) high ste­reocontrol in the rearrangement of 24 to 25. Wannian Zhang and Chunquan Sheng of the Second Military Medical University and Wei Wang of the University of New Mexico and the East China University of Science and Technology added (Org. Lett. 2014, 16, 692) the diketone 26 to the aldehyde 6 to give an intermediate adduct, that further cyclized to 27.
Metal-Mediated C–C Ring Construction: The Carreira Synthesis of (+)-Asperolide C
Authors: Taber Douglass F.
Published: November 2020

Djamaladdin G. Musaev and Huw M. L. Davies of Emory University effected (Chem. Sci. 2013, 4, 2844) enantioselective cyclopropanation of ethyl acrylate 2 with the α-diazo ester 1 to give 3 in high ee. Philippe Compain of the Université de Strasbourg used (J. Org. Chem. 2013, 78, 6751) SmI2 to cyclize 4 to the cyclobutanol 5. Jianrong (Steve) Zhou of Nanyang Technological University effected (Chem. Commun. 2013, 49, 11758) enantioselective Heck addition of 7 to the prochiral ester 6 to give the cyclopentene 8. Liu-Zhu Gong of USTC, Hefei added (Org. Lett. 2013, 15, 3958) the Rh enolate from the enantioselective ring expansion of the α-diazo ester 9 to the nitroalkene 10, to give 11 in high de. Stephen P. Fletcher of the University of Oxford set (Angew. Chem. Int. Ed. 2013, 52, 7995) the cyclic quaternary center of 14 by the enantioselective conjugate addition to 12 of the alkyl zirconocene derived from 13. Alexandre Alexakis of the University of Geneva reported (Chem. Eur. J. 2013, 19, 15226) high ee from the conjugate addition of alkenyl Al reagents (not illustrated) to 12. Paultheo von Zezschwitz of Philipps-Universität Marburg prepared (Adv. Synth. Catal. 2013, 355, 2651) the silyl enol ether 17 by trapping the intermediate from the conjugate addition of 16 to 15. Stefan Bräse of the Karlsruhe Institute of Technology effected (Eur. J. Org. Chem. 2013, 7110) conjugate addition to the prochiral dienone 18 to give the highly substi­tuted cyclohexenone 19. Ping Tian and Guo-Qiang Lin of the Shanghai Institute of Organic Chemistry cyclized (J. Am. Chem. Soc. 2013, 135, 11700) 20 to the kinetic, less stable epimer of the diketone 21. Rh-mediated intramolecular C–H insertion has been a powerful tool for the con­struction of cyclopentane derivatives. Douglass F. Taber of the University of Delaware found (J. Org. Chem. 2013, 78, 9772) that the Rh carbene derived from 22 was dis­criminating enough to target the more nucleophilic C–H bond, leading to the cyclohexanone 23. Kozo Shishido of the University of Tokushima observed (Org. Lett. 2013, 15, 3666) high diastereoselectivity in the intramolecular Heck cyclization of 24 to 25.
Diels–Alder Cycloaddition: Sarcandralactone A (Snyder), Pseudopterosin (−)-G-J Aglycone (Paddon-Row/Sherburn), IBIR-22 (Westwood), Muironolide A (Zakarian), Platencin (Banwell), Chatancin (Maimone)
Authors: Taber Douglass F.
Published: November 2020

En route to sarcandralactone A 3, Scott A. Snyder of Scripps Florida effected (Angew. Chem. Int. Ed. 2015, 54, 7842) Diels–Alder cycloaddition of the activated enone 1 to the Danishefsky diene. On exposure to trifluoroacetic acid, the adduct was unraveled to the ene dione 2. Michael N. Paddon-Row of the University of New South Wales and Michael S. Sherburn of the Australian National University prepared (Nature Chem. 2015, 7, 82) the allene 4 in enantiomerically-pure form. Sequential cycloaddition with 5 followed by 6 gave an adduct that was decarbonylated to 7. Further cycloaddition with nitro­ethylene 8 led to the pseudopterosin (−)-G-J aglycone 9. The protein–protein interaction inhibitor JBIR-22 12 contains a quaternary α-amino acid pendant to a bicyclic core. Nicholas J. Westwood of the University of St. Andrews set (Angew. Chem. Int. Ed. 2015, 54, 4046) the absolute configuration of the core 11 by using an organocatalyst to activate the cyclization of 10. Metal catalysts can also be used to set the absolute configuration of a Diels–Alder cycloaddition. In the course of establishing the structure of the marine natural prod­uct muironolide A 15, Armen Zakarian of the University of California, Santa Barbara cyclized (J. Am. Chem. Soc. 2015, 137, 5907) the enol form of 13 preferentially to the diastereomer 14. Unactivated intramolecular Diels–Alder cycloadditions have been carried out with more and more challenging substrates. A key step in the synthesis (Chem. Asian. J. 2015, 10, 427) of (−)-platencin 18 by Martin G. Banwell, also of the Australian National University, was the cyclization of 16 to 17. In another illustration of the power of the unactivated intramolecular Diels–Alder reaction, Thomas J. Maimone of the University of California, Berkeley cyclized (Angew. Chem. Int. Ed. 2015, 54, 1223) the tetraene 19 to the tricycle 20. Allylic chlo­rination followed by reductive cyclization converted 20 to chatancin 21.
The Fukuyama Synthesis of (−)-Lepenine
Authors: Taber Douglass F.
Published: November 2020

The denudatine alkaloids, exemplified by (−)-lepenine 3, have been converted chem­ically into the physiologically-active aconitine alkaloids. Tohru Fukuyama of Nagoya University envisioned (J. Am. Chem. Soc. 2014, 136, 6598) an intramolecular Mannich condensation, the conversion of 1 to 2, that in a single step would assemble two of the six rings of 3. The starting material for the synthesis was the ether 4, prepared by Mitsunobu cou­pling of the phenol with L-lactic acid methyl ester. Reduction of the ester to the alde­hyde followed by the addition of vinylmagnesium chloride led to the secondary allylic alcohol. Claisen rearrangement with triethyl orthoacetate delivered not the ether, but rather 5, the desired product of an additional Claisen rearrangement. The phenol of 5 was protected as the mesylate, that was then subjected to ozonolysis with a reduc­tive workup to give the primary alcohol. This was protected as the pivalate, which was selectively saponified. The resulting carboxylic acid was cyclized to 6 using trifluoro­acetic anhydride. The triene 7 was prepared from 6 by the addition of vinylmagnesium chloride fol­lowed by dehydration. Prospective intramolecular Diels–Alder cycloadditions that would form five-or six-membered ring lactones often fail. In the event, the cycliza­tion of 7 to the seven-membered ring lactone 8 proceeded smoothly. The tetracyclic 8 could be brought to high ee by recrystallization. Hydroboration followed by reduc­tion then delivered the diol aldehyde 9, that was converted to 1 by reductive amina­tion followed by protection and oxidation. On deprotection, 1 cyclized to the iminium salt 10. Intramolecular Mannich addi­tion of the enol form of the ketone then proceeded, to give 2. It is possible to protect tertiary amines, inter alia by formation of the adduct with a borane. In this case, transient protection as the hydrochloride was sufficient to allow oxidation of the alcohol derived from 2 to the diene 11. This was reactive enough to undergo the Diels–Alder addition of ethylene, from the more open face, leading to 12. The now-extraneous methoxy groups were then removed reductively to give 13, and the last stereogenic center of 3 was installed by hydroboration of the alkene. Methylenation of 14 followed by Luche reduction then completed the synthesis of (−)-lepenine 3.
The Fuwa Synthesis of Didemnaketal B
Authors: Taber Douglass F.
Published: November 2020

Didemnaketal B 3 may be an artifact of isolation, derived from didemnaketal C, in which one of the methyl esters is instead an ethylsulfonate. Nevertheless, it is B, not C, that is a potent inhibitor of HIV protease. Haruhiko Fuwa of Tohoku University has provided (Chem. Eur. J. 2014, 20, 1848) a detailed account of the synthesis of 3, including the necessary revision of the absolute configuration of seven of the stereo­genic centers. A central feature of the modular synthesis of 3 was the cyclization of 1 to the thermodynamically most favorable diastereomer of the spiroketal 2. Three components were combined for the synthesis of 3. The upper sidechain was prepared from commercial citronellal 4. Reduction followed by protection and ozon­olysis delivered the aldehyde 5, that was carried on to the alkyne 6. Hydroiodination using the method previously reported by the authors (OHL May 30, 2011) gave 7, that was oxidized to 8 and then to the ester 9. Lactone formation by ring-closing metathesis is difficult because of the substantial preference for the extended conformation of the ester. As illustrated by the conversion of 10 to 11, this can be overcome by complexation with a Lewis acid. Conjugate addi­tion followed by phosphorylation completed the preparation of the enol phosphate 12. The third component of 3 was the lactone 15, prepared by deprotonation/kinetic protonation with 14 of 13. This was carried on to the sulfone 16, that was coupled with 17. Although the Julia–Kocienski reaction usually strongly favors the E alkene, in this case it was necessary to optimize both the base and the solvent. Sharpless asym­metric dihydroxylation followed by coupling with the enol phosphate 12 then completed the preparation of the diol 1. Addition of the ketene silyl acetal 18 to the aldehyde derived from 2 proceeded to give the undesired diastereomer 19. This was overcome by oxidation to the ketone followed by enantioselective reduction. The iodide 9 was added to the aldehyde 20 to give a 1.8:1 mixture of diastereomers, the major one of which was didemnaketal B 3. This full paper is worth reading in detail. The work reported underlines the impor­tance of powerful protocols for carbon–carbon bond formation that maintain high diastereocontrol in stereochemically complex environments.
The Hoveyda Synthesis of Disorazole C1
Authors: Taber Douglass F.
Published: November 2020

Disorazole C1 3, isolated from fermentation of the myxobacterium Sorangium cellu­losum, shows antifungal and anticancer activity. Amir H. Hoveyda of Boston College applied (J. Am. Chem. Soc. 2014, 136, 16136) recent advances in alkene metathesis from his group to enable the efficient assembly of 2 and so of 3. The ester 1 was assembled from the alcohol 11 and the acid 18. The preparation of 11 began with the enantioselective addition of 5 to 4 to give 6 and then 7, as described by Kalesse (Angew. Chem. Int. Ed. 2010, 49, 1619). Leighton allylation led to 8, that was then coupled with 9 to give 10 with high Z selectivity. Iodination of 10 followed by deprotection then completed the assembly of 11. The starting material for the acid 18 was the allylic alcohol 13. As reported by Cramer (Angew. Chem. Int. Ed. 2008, 47, 6483), exposure of the racemic alcohol 12 to vinyl acetate in the presence of Amano lipase PS converted one enantiomer to the acetate, leaving 13. Methylation of the secondary alcohol followed by acid-mediated removal of the t-butyl ester led to the acid 14, that was converted to the correspond­ing acyl fluoride and coupled with serine Me ester 15 to give 16. After cyclization to the oxazole 17, cross metathesis with five equivalents of 4-bromo-1-butene gave the homoallylic bromide, that was readily eliminated with DBU to give, after saponifica­tion, the acid 18. The cross metathesis of the coupled ester 1, a polyene, with 9 proceeded with remarkable selectivity to give 2, again as the Z geometric isomer. On exposure to the Heck catalyst Pd [(o-tolyl)3P]2, 2 dimerized efficiently. The deprotection was not straightforward, but conditions (H2SiF6, CH3OH, 4°C, 72 h) were found that deliv­ered 3 in 68% yield.
Condensation Reactions Synthesize Random Polymers
Authors: Ross David
Published: November 2020

Over the past half century of serious research on the origin of life, several schools of thought have emerged that focus on “worlds” and what came first in the pathway to the origin of life. One example is the RNA World, a term coined by Walter Gilbert after the discovery of ribozymes. Other examples include the Iron-Sulfur World of Günther Wächtershäuser and the Lipid World proposed by Doron Lancet and coworkers. Then we have a competition between “metabolism first” and “replication first” schools. The worlds and schools have the positive effect of sharpening arguments and forcing us to think carefully, but they also can lock researchers into defending their individual approaches rather than looking for patterns in a larger perspective. One of the main themes of this book is the notion that the first living cells were systems of functional polymers working together within membranous compartments. Therefore, it is best not to think of “worlds” and “firsts” as fundamentals but instead as components evolving together toward the assembly of an encapsulated system of functional polymers. At first the polymers will be composed of random sequences of their monomers, and the compartments will contain random assortments of polymers. Here, we refer to these structures as protocells which are being produced in vast numbers as they form and decompose in continuous cycles driven by a variety of impinging, free-energy sources. This chapter describes how thermodynamic principles can be used to test the feasibility of a proposed mechanism by which random polymers can be synthesized. There is a current consensus that early life may have passed through a phase in which RNA served as a ribozyme catalyst, as a replicating system, and as a means for storing and expressing genetic information. For this reason, we will use RNA as a model polymer, but condensation reactions also produce peptide bonds and oligopeptides. At some point in the evolutionary steps leading to life, peptides and RNA formed complexes with novel functional properties beyond those of the individual molecular species.
Cycles, Compartments, and Polymerization
Authors: Deamer David W.
Published: November 2020

The two quotes in the epigraph, in juxtaposition, always make me smile, and I tried to keep them in mind while writing this chapter. The first eight chapters of this book have the effect of eliminating the impossible by investigating the facts to which Twain is referring. Perhaps he would consider them trifling, but I doubt that Twain ever performed an experiment to test an idea. Every working scientist knows that science is not just a set of facts but is also a set of questions. The best way to begin answering a question is to pose a hypothesis and that hypothesis begins as a conjecture. Only when we have a hypothesis, can we design experiments to test it, and if we are lucky, the results of those experiments lead us a little closer to the truth. This chapter summarizes facts that lead to an alternative scenario for life’s origin in freshwater hydrothermal conditions rather than a marine origin in saltwater hydrothermal vents. As stated in the introduction to this book, when assumptions are part of the story they will be made explicit so that the logic that arises from them will be clear. What follows in this overview is a list of ten prerequisites we assume are necessary for cellular life to begin, followed by eight assumptions underlying the scenario to be presented here. Prerequisite conditions for life to begin: Dilute solutions of potential reactants are available, together with a process by which they can be sufficiently concentrated to react. Energy sources available in the environment can drive reactions such as carbon fixation, primitive metabolism, and polymerization. Products of reactions accumulate within the site rather than dispersing into the bulk phase environment. Amphiphiles assemble into membranous compartments over the range of temperatures, salt concentrations, and pH values related to each site. Biologically relevant polymers are synthesized with chain lengths sufficient to act as catalysts or incorporate genetic information. A plausible physical mechanism can produce encapsulated polymers as protocells then subject them to combinatorial selection. Organic solutes in aqueous solutions become biochemical solutes within protocells and then substrates supporting a primitive metabolism.
The First Meeting
Authors: Rosenstein Donald L. , Yopp Justin M.
Published: November 2020

Dan had been terrified of speaking in front of people for as long as he could remember. As a child, he avoided eye contact with teachers so they wouldn’t call on him in class and he insisted on non-speaking parts when he had to participate in school plays. In high school, he feigned stomachaches to avoid giving class presentations and never dared to run for student council. Over time, Dan’s fear of embarrassment shaped his personality. He was shy and introverted, and he stayed away from situations that invited scrutiny. Naturally, when Dan first heard about a new support group for recently widowed fathers, he thought there was no way he could join. Opening up to a room full of strangers about his wife’s illness and recent death was nightmare material. It was precisely the kind of situation he had spent a lifetime avoiding. Still, Dan knew that he needed some kind of help. He had been in bad shape in the months since his wife had died. He felt isolated in his grief and overwhelmed by the prospect of raising two children by himself. As Dan saw it, his kids not only lost their mother but were now stuck with a father whose ineptitude as a parent was only making things worse: a cruel “double-whammy.” Despite his fears, he decided to join the support group because he felt he owed it to his children to be a better parent. Dan set the bar low for that first night: show up, sit quietly, listen to the other fathers, and avoid drawing attention to himself. If asked to share his story, he would offer only the barest of details. If called on to participate in group discussion, he would keep his input to a minimum. As he pulled into the parking lot for the first meeting, Dan felt a familiar wave of anxiety. His stomach churned and his heart began to pound. He thought about turning back. Instead, Dan closed his eyes and tried to calm down. After ten minutes, he took a deep breath and stepped out of the car.
Ethics, Morals, and Ethical Theory
Authors: Kovac Jeffrey
Published: November 2020

In ordinary language, the words ethics and morals are used interchangeably to refer to standards of conduct or social norms that guide proper behavior. The English ethics derives from the Greek ethika, meaning character or custom, and is related to the Latin mores, also meaning custom, which gave us the word moral. Some philosophers, however, distinguish between the two. Morals is often taken to refer to universal norms of human behavior—the distinction between good and evil—whereas ethics is used as a generic term for all the different ways scholars use to understand and examine our moral lives (Beauchamp and Childress 2001). Some approaches to ethics are normative while others are nonnormative. Normative approaches seek to discover and justify the general standards of be­havior we should accept, and to apply them to specific situations. Nonnormative approaches can be descriptive—that is, factual investigations of moral con­duct and belief—or what is called meta-ethics, the analysis of ethical language, concepts, and methods of reasoning. Morality generally refers to norms for right and wrong human conduct that are so widely shared they form a stable social consensus. Here it is important to distinguish between what many philosophers call the common morality, the norms that all serious persons share, and communal norms that are shared only by a specific community. Common morality, although it cannot be specified precisely, is universal. Communal norms are similar to the common morality but are specific to a particular group, like a religious or cultural community. Common morality also includes moral ideals and extraordinary virtues, which call us to exhibit morally exemplary behavior. Common morality seems to spring from human nature as shaped by living together in community. Successful communal life requires that people adhere to certain standards of behavior. For example, a principle of promise keeping seems essential to any society, whatever its specific organization. Similarly, the arbitrary harming or killing of other people cannot be tolerated in a civilized society. A principle of truth telling seems essential to all human relationships.
Professionalism and Ethics in Chemistry
Authors: Kovac Jeffrey
Published: November 2020

Common morality and ethical theory are universal. Not only do they provide the standards of conduct that we expect all rational persons to follow, but also they provide the basis for professional ethics, the special rules of conduct adhered to by those engaged in pursuits ordinarily called professions, such as law, medicine, engineering, and science. Although common morality and ethical theory are general, professional ethics is specific. Legal ethics applies only to lawyers (and no one else); scientific ethics applies only to scientists. Professional ethics is consistent with common morality, but goes beyond it. Professional ethics governs the interactions among professionals, and between professionals and society (Callahan 1988). In many cases, it requires a higher standard of conduct than is expected of those outside the profession, but the norms of professional ethics must be consistent with common morality. To understand professional ethics, it is necessary to understand the concept of a profession (Davis 1998). A profession is more than a group of people engaged in a common occupation for which they are paid. While there are a variety of ways to define a profession, I use a social contract approach, which I have found to be most useful in my thinking about professional ethics. In this view, a profession derives from two bargains or contracts: one internal and one external. The internal bargain governs the interactions among members of the profession while the external bargain defines the relationship of the profession to society. Both, however, are based on a moral ideal of service around which the profession is organized (Davis 1987). For lawyers, the ideal is justice under law. For physicians, the ideal is curing the sick, protecting patients from disease, and easing the pain of the dying. As Michael Davis has argued, these moral ideals go beyond the demands of ordinary morality, the requirements of law, and the pressures of the market. Using a moral ideal as the fundamental basis of the profession comes from the old- fashioned idea of a profession as a calling.
Griffin’s Quest
Authors: Colby Jason M.
Published: November 2020

By the early spring of 1962, all of western Washington was abuzz with Seattle’s upcoming world’s fair—the first to be held in the United States since 1940. On April 21, with the push of a button in the Oval Office, President John F. Kennedy released a swarm of balloons 2,300 miles away in Seattle. Seconds later, warplanes from the naval air station on nearby Whidbey Island roared over the city, thrilling the throngs of eager fairgoers. Over the next six months, nearly ten million people passed through the turnstiles, among them Elvis Presley, to film his forgettable It Happened at the World’s Fair (1963). Officially titled the Century 21 Exposition, the fair boasted exhibits from twenty-seven countries and a range of attractions. But with futuristic highlights such as the Monorail and Space Needle, it aimed above all to celebrate Seattle’s new modern identity. It seemed the perfect theme for the time and place. Just two months earlier, John Glenn had become the first American to orbit the earth, and the Cold War space race was in full swing. The Boeing Company, with its headquarters and three manufacturing plants in and around the city, was a leader in cutting-edge commercial and military aviation. If the 1962 world’s fair didn’t launch Seattle into the twenty-first century, it certainly signaled the city’s move away from its nineteenth-century extractive economy. But these changes came at a cost. Seattle’s maritime industries had been declining since World War II, even as Boeing jobs and freeway construction hastened flight to the suburbs. By the early 1960s, city leaders were pushing for urban renewal. The Seattle Times led the way, publishing a special feature in October 1961 that called for a “downtown for people.” To be sure, the Century 21 Exposition provided a short-term boost, drawing visitors to the fair site at the base of Queen Anne Hill and creating the new tourist hub of Seattle Center. But two months later, an event drew visitors to the waterfront itself.
Namu’s Journey
Authors: Colby Jason M.
Published: November 2020

The call came by ship-to-shore radio from a Washington State ferry. The skipper on the Seattle-Bremerton route had just spotted killer whales headed south, and he thought Ted Griffin should know. Shouting his thanks, the aquarium owner raced down the dock, leapt into Pegasus, and tore off in the direction of the sighting. Clocked at sixty miles per hour, the shallow-draft runabout may have been the fastest boat on Puget Sound, and it overtook the orcas near Vashon Island. But as Griffin throttled down, he realized to his disbelief that someone else was already chasing them. There, clear as day, was a blue helicopter hovering over the whales. Incensed, Griffin steered Pegasus closer, until he could almost touch the helicopter’s pontoons. Looking up, he spotted a burly man leaning out the cabin door and eying the pod. “Get away from my whales!” Griffin shouted. “Your whales?” the man laughed. “You’ll have to catch them first.” It was the first time Griffin had met Don Goldsberry, ex-fisherman and animal collector for the Point Defiance Aquarium (formerly the Tacoma Aquarium). The two men’s shared pursuit of orcas would soon bind them together. On this day, however, Griffin left feeling a bit embarrassed, having behaved, as he put it, “like a rancher possessive of his herd.” Some part of him knew his quest to capture and befriend a killer whale was becoming unhealthy. He had a struggling aquarium in Seattle and a growing family on Bainbridge Island. Orcas were his obsession, but they weren’t paying the bills. At home, he still talked and laughed with Joan and played with his little sons, Jay and John. But he had whales on the brain. He dreamed of them when asleep and sometimes mumbled about them when awake. With each reported sighting, he dropped everything—to Joan’s increased annoyance. In time, Griffin had come to see patterns in the animals’ migrations and behavior. He noted that they appeared when chinook salmon were running and that they seemed to cling to the west side of Puget Sound when headed south and to the east side when swimming north.
The Whales of Pender Harbour
Authors: Colby Jason M.
Published: November 2020

By early 1968 , Cecil Reid Jr. had given some thought to orcas. A gill net fisherman based in Pender Harbour, the thirty-one-year-old Reid—“Sonny” to his friends—had seen many killer whales over the years. As a boy growing up in the 1940s, he heard locals grumble about blackfish, and he watched family members take shots at the animals as they passed by. “My grandfather lived out around the corner from Irvine’s Landing,” he recalled, “and when the whales showed up, they would get the guns out and start shooting them.” Yet Reid knew live killer whales had become lucrative commodities, and when his father suggested catching one, he decided to give it a try. It was winter, however, and there weren’t many orcas around. Then, to his surprise, they came to him. In the late afternoon of Wednesday, February 21, a pod wandered into Pender Harbour, passing Reid’s waterfront home on Garden Bay. Momentarily stunned, Reid raced down to his boat, Instigator One. “I just happened to have my San Juan net still on the drum—which is a lot deeper and touched bottom,” he later recounted. “So when they came into Garden Bay the first time, I just set my net across.” The whales eluded his first attempt, but they lingered in the harbor, and the following morning Reid convinced other fishermen to help him, including several of his brothers and members of the local Cameron and Gooldrup families. In all, nine fishermen worked to seal off Garden Bay, and as the sun set over Irvine’s Landing, Reid felt certain they had trapped at least three orcas. But that night, one of the nets tore loose, and in the morning only one whale remained. Disappointed, Reid and his partners secured the animal—a fifteen-footer they believed to be male. Like those caught previously, the trapped orca hesitated to challenge the frail net surrounding him, much to the fishermen’s relief. Within minutes, the animal was swimming placidly in its makeshift enclosure. “Maybe it likes it here,” mused Reid.
Misbehavior and behavior
Authors: Bennett Peggy D.
Published: November 2020

Student misbehavior has the power to make our lives miser­able, derail our lessons, and convince us that we should not be teachers. Whether we are early- , mid- , or late- career educa­tors, few experiences in life rob us of our peace of mind to the extent that student misbehaviors do. Sometimes our attempts to manage student behavior prob­lems cause us to become so hypervigilant that we turn into pouncers. We jump on any potential behavioral infraction we see, and that becomes our habit. Always watchful in order to stave off unruly behavior, we can become harsh, unyielding, and strident in our attempts to keep students “under control.” Yet what if we’re wrong about misbehavior? What if it’s not what we think it is? One of the most profound changes we can make in our teach­ing comes from a very simple idea, a unique definition of misbe­havior. Educational psychologist C. M. Charles tells us that only when behavior is knowingly and willingly obstructing is it misbe­havior (Charles, 1985, p. 4). Could it be true that most of what we see in schools is simply behavior? Reinterpreting behaviors initially takes some effort, but it is well spent. Soon such reinterpretation becomes automatic. The habit of seeing behavior first as simply behavior gives us pause. And that pause allows us to craft our verbal and emotional responses. • We more often retain a calm internal and external counte­nance. This calm allows us to address the behavior and the consequence matter- of- factly and without accusation. • We respond with the appropriate level of assertiveness and direction. • We give a moment of grace to neutrally identify what we see and hear. • We explain calmly and assertively why the behavior needs to change. Consider this. Sometimes we adults are rude, annoying, unfair, rough, or vulgar. Are we misbehaving? Is our misbehavior worthy of punishment? When we give up assuming intent, it changes us. We may choose not to ignore the behavior, but we also do not presume malicious or disrespectful intent.
Acknowledging boundaries
Authors: Bennett Peggy D.
Published: November 2020

We all have boundaries. The limit at which our yes turns to no defines our sense of “crossing the line.” Yet others may not have the same lines. Language usage, physical contact, attire, and academic integrity are some of the categories that can incite a sense of boundary violation. Yet we have an obligation to inform. “Knowing and showing” our boundaries can help pre­vent boundary violations that embarrass and wound. What boundaries do we take to school? What boundaries do our school policies expect from us? Do we enter school with sen­sitivities toward others’ personal spaces and preferences? Are we careful (full of care) about intruding on others’ beliefs and social comfort? For some, asking personal questions, sharing private infor­mation, using profanity, and name- calling cross the lines of acceptability. To function within clear boundaries, we may need to inform others of behavior that makes us uncomfortable. Depending on our level of discomfort, we may need to esca­late our responses from cordial conversations to matter- of- fact opinions and eventually to strong “cease and desist” stances. Choosing an appropriate level of intensity makes clear our expectations for boundaries. If we do not inform others, we can­not justifiably hold them accountable for what they do not know. When we know our boundaries and when we respect the boundaries of others, we have a much greater chance of prop­erly, sensitively, and comfortably orienting ourselves in schools. Knowing and living our boundaries develops a healthy trust in ourselves. We need not be haughty or apologetic when we reveal our discomfort with words or behaviors: “I won’t cross that line.” “I can’t be party to this discussion.” “I’m exceed­ingly uncomfortable with this conversation.” “She has a right to expect that conversation to be kept private.” “I believe there are some ethical issues to be considered with this situation.” Dubious behaviors can too easily become unexamined hab­its. Once a state of mutual trust is breached, returning to that state can take time, effort, and commitment. Knowing and show­ing school- appropriate boundaries can help everyone.
The virtue of listening
Authors: Bennett Peggy D.
Published: November 2020

In schools, we listen. We listen to discoveries. We listen to tensions. We listen to revelations. Listening informs us about others and about ourselves. At the heart of teaching, there is listening. How good are we at listening? Do we give the speaker our full attention? Some of us specialize in distracted listening. We veer off course. We drift as we “listen” to a student telling us about his important news. We plan our lesson as we “listen” to lunchroom talk. We craft our rebuttal as we “listen” to someone disagreeing with us. As with so many other behaviors, our listening can have wide ranges of intensity. We can become so absorbed in our school duties that we develop a habit of not listening. Often, it seems, listening becomes a casualty of multitask­ing: “listening” as we grade papers, read an announcement, straighten our room. Yet news has also reached us that multitask­ing may not be as desirable as or effective as we think. When do we still our minds and bodies to just listen? • When a student expresses frustration in completing an assign­ment or learning task, gently “ask, listen, and learn” about the obstacle she is facing. • When a parent is worried about his child’s behavior, “ask, listen, and learn” to best formulate your compassionate response. • When a committee is at odds about projected changes, set the tone by “asking, listening, and learning” to further the goals of mutual, respectful problem- solving. When we infuse our schools with active listening and respon­sive commentary, we upgrade our levels of vitality and vigor. We supplant the detached “surface listening” with active, quizzical listening that provides real communication, real connection. As an experiment, devote one day to attentive, focused lis­tening at school. Notice what happens on your “listening day.” Any time you can demonstrate your willingness to listen to someone with a minimum of self- defensiveness or criticism, you are cultivating virtues within yourself that have a high payoff in self- respect.
My word!
Authors: Bennett Peggy D.
Published: November 2020

Name- calling and use of offensive words appear to be increas­ingly acceptable in our communities and in our entertain­ment venues. Offensive words have no place in schools. Yet how do we know what is offensive, especially across diversities of age, family values, and ethnicity? We can become immune to com­monly used expletives, even when teachers hold themselves to a higher standard than the general public. The intent in questioning some words and sayings here is two­fold: to make us aware of our sometimes automatic responses and to encourage attention to and reconsideration of words and phrases we may be using in schools. • Inflammatory words may be so commonly overused that they lose their shock effect: “loser,” “jerk,” “bully,” “predator,” “troublemaker,” “dumb,” “harasser,” “racist.” Nonetheless, name- calling is risky, hurtful, and confrontational. • Slogans and sayings that at one time were novel and clever can be overused and lose their potency. When phrases become too repetitive and too predictable, students can be repelled by them rather than attentive to them. One example was a junior high school principal who, during every school assem­bly, would step to the microphone and drone, “We’re waiting on you!” The too- predictable admonition was rarely, if ever, effective. Other examples could be “Crisscross applesauce” when we want students to sit cross- legged on the floor, “I’m the teacher, you’re the listener,” and “No pain, no gain.” • Offensive words can sometimes be defused by probing a bit about what a student or teacher means: “What does that word mean?” “Can you tell me why you’re using that word?” “That word produces a strong reaction in me.” It is natural and valuable to react to language. We can hardly pre­vent it. It is our primary and primal avenue for communication. Yet it is good for us as teachers to pay attention. It is smart to reflect on the meaning and the impacts of the words we say and hear. It is wise to be informed and purposeful with our vocabu­lary in schools.
Just breathe
Authors: Bennett Peggy D.
Published: November 2020

“Just breathe.” Two very potent words. We may hear them when we are anxious or fretting. We may silently speak them when we yearn for tranquility. In and out . . . the power of that simple practice of breath­ing is palpable. Breathe in slowly through your nose to gather strength, wisdom, and calm. Breathe out slowly through your mouth to release weakness, confusion, and threat. The power of breath offers calm and restores vigor in ways large and small. • Breathing can dissipate and dissolve apprehension. • Breathing can muster our best intentions. • Breathing can project our voices without harshness or stridency. • Breathing can create soft eyes that project calm. • Breathing can shift frenzy to composure. • Breathing can give us the calm that we need to choose our responses carefully. • Breathing can reinvigorate our mind and spirit. You feel nervous before teaching a new lesson about which you are not fully confident. Just breathe. You are summoned to speak to the principal about a thorny issue involving another teacher, and you are worried about what to say. Just breathe. A parent stridently lets you know that your teaching does not measure up to his expectation. Just breathe. When you need to summon your strongest rather than your most vulnerable self, just breathe. Though chest breathing has now become natural and invol­untary for most of us, it is really a part of the fight/ flight syndrome, aroused when the organism is challenged by some external stress or danger. Because of the reciprocity between breath and mind, chest breathing, in turn, gives rise to the tension and anxiety associated with fight/ flight syndrome. With chest breathing, the breath is shallow, jerky and unsteady, resulting in similar unsteadiness of the mind. All techniques aimed at providing relaxation of the body, nerves and mind will be ineffective unless chest breathing is replaced by deep, even and steady diaphragmatic breath­ing.
Students being friends
Authors: Bennett Peggy D.
Published: November 2020

Until recently, “friend” was a beloved term. Signifying an affectionate bond, shared memories, and trusted commu­nications, “friend” was an honorable designation, representing a personal alliance that included fondness. Simply “knowing someone” has not traditionally constituted a friendship. Do we try too hard to force student friendships? Do we label students our friends, even though we know better? Do we muddy the roles in schools and mislabel relationships when we try too hard to promulgate connections and bonds? Reconsider telling students who their friends are. Especially in younger grades, some teachers refer to all classmates as “friends”: “Choose a friend to be your partner.” “Check with your friends and make a choice.” “Are all our friends present?” “My friends, are you all ready to begin our lesson?” When we use “friend” as a synonym for “classmate,” we may be designating a relationship that does not exist. Teacher- orchestrated friendships can be both risky and confusing as stu­dents are developing their often fragile social connections Rethinking the ways we use the term “friends” in our class­rooms is worth reflection. Some students merely become confused when a teacher says, “These are your three friends for this activity.” Others may become resentful and angry. The social milieu of schools is both delicate and sturdy. What might be gained if we help students understand the differences between being a friend and being friendly? How might students benefit from knowing what being a friend means and what being friendly looks like? Rather than telling stu­dents (or anyone else) that they are friends, we can encourage them to be friendly. We can let them see where their preferences for friendships take them.
Teacher as entertainer
Authors: Bennett Peggy D.
Published: November 2020

Some educators become troubled when they watch award ceremonies for teachers and news segments about schools. Very often in those settings, videos show teachers engaged in dramatic, highly animated activity. Nearly all have bold person­alities, and students’ enthusiasm can verge on frenetic. Why might educators be troubled about these images of education? Because the implicit message seems to be that full- throttle dramatic behavior equates with teaching. That groups jumping and shouting equates with learning. Animation can be delivered on a sliding scale that we turn up or turn down, based on students’ learning needs and desires. Varying intensities of verbal and nonverbal communication are important for all teachers to master. Vocal expression and vol­ume, posture, eye contact and expression, gestures, movement, and proximity— all are behaviors that contribute to our animation and teaching personae. If we generate all the energy and excitement in the room, we may be missing out on helping all our students learn. If we treat teaching as entertainment, as our performance of the lesson, we may be missing out on learning how our students learn. Variation in intensities and types of animation is pedagogi­cally sound and educationally warranted. Quiet and calm may need infusions of bold and invigorated. Boisterous and loud may need times of peaceful and hushed . . . all for the benefit of stu­dent learning. A self- check may help us reflect on teaching tendencies and ponder the point at which our entertainer personalities may be subduing students’ learning. • Are we the primary generator of ideas during our classes? • Do we rely on quips, jokes, and teasing to engage students? • Does our level of animation and drama drive the class and the lesson? • Does the proportion of our teacher- talk greatly outweigh student- talk? • Do we value quiet, hesitant student contributions as much as eager, enthusiastic ones? It is every teacher’s challenge to notice and adapt for the benefit of students. Whether our comfort lies in being “a sage on the stage” or “a guide at the side,” we know that we likely need to do both for the benefit of students’ learning.