An Enantioselective Total Synthesis of (+)-Duocarmycin SA.
Schmidt, Michael A.; Simmons, Eric M.; Wei, Carolyn S.; Park, Hyunsoo; Eastgate, Martin D.; The Journal of organic chemistry 83 (2018) 3928–3940; doi:10.1021/acs.joc.8b00285

data_4033557
_publ_section_title
;
 An Enantioselective Total Synthesis of (+)-Duocarmycin SA.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3928
_journal_page_last               3940
_journal_paper_doi               10.1021/acs.joc.8b00285
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H37 N O4 S Si'
_chemical_formula_sum            'C29 H37 N O4 S Si'
_chemical_formula_weight         523.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 102.756(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3043(7)
_cell_length_b                   22.8190(16)
_cell_length_c                   15.8252(12)
_cell_measurement_reflns_used    9834
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      63.73
_cell_measurement_theta_min      2.86
_cell_volume                     2924.8(4)
_computing_cell_refinement       'Bruker APEX 3 (2017)'
_computing_data_collection       'Bruker APEX 3 (2017)'
_computing_data_reduction        'Bruker APEX 3 (2017)'
_computing_molecular_graphics    'Mercury 3.8 (2016)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  platform
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49506
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        63.885
_diffrn_reflns_theta_max         63.885
_diffrn_reflns_theta_min         2.863
_diffrn_source                   'Microfocusing source'
_diffrn_source_type              'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    1.636
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       rod
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.150
_refine_diff_density_max         1.231
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 4062 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     660
_refine_ls_number_reflns         9485
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0609
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0950P)^2^+2.0664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1698
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                8909
_reflns_number_total             9485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00285_si_002.cif
_cod_data_source_block           compound4
_cod_depositor_comments
'Adding full bibliography for 4033557--4033558.cif.'
_cod_database_code               4033557
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.648
_shelx_estimated_absorpt_t_max   0.791
_shelx_res_checksum              79902
_shelx_hkl_checksum              87639