Stereoselective synthesis of F-ring saturated estrone-derived inhibitors of Hedgehog signaling based on cyclopamine.
Zhang, Zhihui; Baubet, Valérie; Ventocilla, Christian; Xiang, Chaomei; Dahmane, Nadia; Winkler, Jeffrey D.; Organic letters 13 (2011) 4786–4789; doi:10.1021/ol2017966

data_1502401
_publ_section_title
;
 Stereoselective synthesis of F-ring saturated estrone-derived inhibitors
 of Hedgehog signaling based on cyclopamine.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4786
_journal_page_last               4789
_journal_paper_doi               10.1021/ol2017966
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_sum            'C38 H41 N3 O7'
_chemical_formula_weight         651.74
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.570(3)
_cell_angle_beta                 91.750(3)
_cell_angle_gamma                108.864(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1374(3)
_cell_length_b                   10.4915(5)
_cell_length_c                   23.5245(12)
_cell_measurement_temperature    143(1)
_cell_volume                     1651.72(14)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            28283
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.869
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     869
_refine_ls_number_reflns         5852
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0796P)^2^+0.5682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1375
_reflns_number_gt                5268
_reflns_number_total             5852
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2017966_si_005.cif
_cod_data_source_block           twin51
_cod_original_cell_volume        1651.72(13)
_cod_original_sg_symbol_H-M      'P 1       '
_cod_database_code               1502401