Efficient Formal Synthesis of (±)-Hyphodermin B
Luke C. Henderson; Wendy A. Loughlin; Ian D. Jenkins; Peter C. Healy; Marc R. Campitelli; Journal of Organic Chemistry 71 (2006) 2384–2388; doi:10.1021/jo052485l

data_4021557
_publ_contact_author_address
;
School of Science
Eskitis Institute
Griffith University
Nathan, BRISBANE 4111, Australia
;
_publ_contact_author_email       P.Healy@griffith.edu.au
_publ_contact_author_fax         '617 3735 7656'
_publ_contact_author_name        'Dr Peter Healy'
_publ_contact_author_phone       '617 3735 7442'
_publ_section_title
;
 Efficient Formal Synthesis of (+-)-Hyphodermin B
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2384
_journal_page_last               2388
_journal_paper_doi               10.1021/jo052485l
_journal_volume                  71
_journal_year                    2006
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C14 H14 O4'
_chemical_formula_sum            'C14 H14 O4'
_chemical_formula_weight         246.25
_chemical_name_common            'Hypodermin B'
_chemical_name_systematic
; 
1RS-Hydroxy-6,6-dimethyl-7,8-dihydronaphtho[1,2-c]furan-3,9(1H,6H)-dione 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 91.00(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.937(5)
_cell_length_b                   7.227(3)
_cell_length_c                   10.649(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      17.2
_cell_measurement_theta_min      12.6
_cell_volume                     1226.3(7)
_computing_cell_refinement       'MSC/AFC7 Diffractometer Control (MSC, 1999)'
_computing_data_collection       'MSC/AFC7 Diffractometer Control (MSC, 1999)'
_computing_data_reduction        'teXsan for Windows (MSC, 2001)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material
'teXsan for Windows (MSC, 2001); PLATON (Spek, 2003)'
_computing_structure_refinement
'teXsan for Windows (MSC, 2001); SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'teXsan for Windows (MSC, 2001)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Rigaku AFC7R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2467
_diffrn_reflns_reduction_process ' ?'
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        0.19
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0666
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1048P)^2^+0.6808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.2182
_reflns_number_gt                1241
_reflns_number_total             2163
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo052485lsi20060208_112004.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4021557