Enantioselective total synthesis of (+)-brazilin, (-)-brazilein and (+)-brazilide A
Xuequan Wang; Hongbin Zhang; Xiaodong Yang; Jingfeng Zhao; Chengxue Pan; Chem.Commun. 49 (2013) 5405–; doi:10.1039/c3cc42385a

data_7109365
_publ_section_title
;
 Enantioselective total synthesis of (+)-brazilin, (-)-brazilein and
 (+)-brazilide A
;
_journal_name_full               Chem.Commun.
_journal_page_first              5405
_journal_paper_doi               10.1039/c3cc42385a
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H14 O7, C3 H6 O'
_chemical_formula_sum            'C19 H20 O8'
_chemical_formula_weight         376.35
_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                 111.3280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.9939(2)
_cell_length_b                   6.73910(10)
_cell_length_c                   12.6864(3)
_cell_measurement_reflns_used    7065
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.00
_cell_measurement_theta_min      3.74
_cell_volume                     875.55(3)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7274
_diffrn_reflns_theta_full        68.19
_diffrn_reflns_theta_max         68.19
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  0.9280
_exptl_absorpt_correction_T_min  0.5819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.36(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2361
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0278
_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^)+(0.0376P)^2^+0.1735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0719
_reflns_number_gt                2354
_reflns_number_total             2361
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc42385a.txt
_cod_data_source_block           cu_zhb_w_1_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7109365