Total Syntheses of the Phytotoxic Lactones Herbarumin I and II and a Synthesis-Based Solution of the Pinolidoxin Puzzle
Alois Fürstner; Karin Radkowski; Conny Wirtz; Richard Goddard; Christian W. Lehmann; Richard Mynott; Journal of the American Chemical Society 124 (2002) 7061–7069; doi:10.1021/ja020238i

data_4114890
_publ_section_title
;
 Total Syntheses of the Phytotoxic Lactones Herbarumin I and II and a
 Synthesis-Based Solution of the Pinolidoxin Puzzle
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7061
_journal_page_last               7069
_journal_paper_doi               10.1021/ja020238i
_journal_volume                  124
_journal_year                    2002
_chemical_compound_source        'see paper'
_chemical_formula_moiety         'C24 H26 Br2 O6'
_chemical_formula_sum            'C24 H26 Br2 O6'
_chemical_formula_weight         570.27
_chemical_name_systematic
; 
 (2R,3S,4S)-2,3-((1-methylethylidene)-dioxy)-1,4-O-p-bromobenzoyloxy-heptane
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 108.2090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.7691(2)
_cell_length_b                   5.71680(10)
_cell_length_c                   18.3157(2)
_cell_measurement_reflns_used    11039
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.14
_cell_measurement_theta_min      1.96
_cell_volume                     1170.60(3)
_computing_cell_refinement       'Denzo / Scalepack (Otwinowski 1997)'
_computing_data_collection       'Collect software (Nonius, 1998)'
_computing_data_reduction        'Denzo / Scalepack (Otwinowski 1997)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD \w-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.3 mm focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10839
_diffrn_reflns_theta_full        33.12
_diffrn_reflns_theta_max         33.12
_diffrn_reflns_theta_min         4.69
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.500
_exptl_absorpt_correction_T_max  0.93828
_exptl_absorpt_correction_T_min  0.69455
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'XPREP, Siemens (1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.681
_refine_diff_density_min         -1.293
_refine_diff_density_rms         0.177
_refine_ls_abs_structure_details 'Flack, H. D. (1983). Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         6488
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.2782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                6080
_reflns_number_total             6488
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja020238i_4.cif
_cod_data_source_block           4043
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4114890