Catalytic Enantioselective Total Synthesis of (-)-Platyphyllide and Its Structural Revision
Shiharu Hiraoka; Shinji Harada; Atsushi Nishida; Journal of Organic Chemistry 75 (2010) 3871–3874; doi:10.1021/jo1003746

data_4025447
_publ_section_title
;
 Catalytic Enantioselective Total Synthesis of (-)-Platyphyllide and Its
 Structural Revision
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3871
_journal_page_last               3874
_journal_paper_doi               10.1021/jo1003746
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C25 H31 Br O8 S'
_chemical_formula_weight         571.47
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.33(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.352(14)
_cell_length_b                   7.528(14)
_cell_length_c                   45.19(8)
_cell_measurement_reflns_used    820
_cell_measurement_temperature    296
_cell_measurement_theta_max      16.56
_cell_measurement_theta_min      2.70
_cell_volume                     2501(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_sigmaI/netI    0.1627
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            7244
_diffrn_reflns_theta_full        20.21
_diffrn_reflns_theta_max         20.21
_diffrn_reflns_theta_min         1.35
_exptl_absorpt_coefficient_mu    1.775
_exptl_absorpt_correction_T_max  0.9165
_exptl_absorpt_correction_T_min  0.7178
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         4640
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1656
_refine_ls_wR_factor_ref         0.1940
_reflns_number_gt                3468
_reflns_number_total             4640
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1003746_si_002.cif
_cod_data_source_block           harada100410p21
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025447