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_4033558
_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         'C25 H23 N3 O7'
_chemical_formula_sum            'C25 H23 N3 O7'
_chemical_formula_weight         477.46
_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                 91.462(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2955(5)
_cell_length_b                   14.6854(6)
_cell_length_c                   12.6900(6)
_cell_measurement_reflns_used    5792
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      47.77
_cell_measurement_theta_min      3.48
_cell_volume                     2290.62(17)
_computing_cell_refinement       'Bruker APEX 3 (2016)'
_computing_data_collection       'Bruker APEX 3 (2016)'
_computing_data_reduction        'Bruker APEX 3 (2016)'
_computing_molecular_graphics    'Mercury 3.9 (2016)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  kappa
_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  0.0709
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19174
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        47.875
_diffrn_reflns_theta_max         47.875
_diffrn_reflns_theta_min         3.484
_diffrn_source                   'Rotating anode'
_diffrn_source_type              'Bruker MicroStarH'
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  0.7494
_exptl_absorpt_correction_T_min  0.6135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
_exptl_crystal_recrystallization_method DCM-hexanes
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1350 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         4209
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0965P)^2^+0.9673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1496
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                3425
_reflns_number_total             4209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00285_si_002.cif
_cod_data_source_block           duocarmycin
_cod_depositor_comments
'Adding full bibliography for 4033557--4033558.cif.'
_cod_database_code               4033558
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.795
_shelx_estimated_absorpt_t_max   0.950
_shelx_res_checksum              78825
_shelx_hkl_checksum              93347