Enantioselective Total Synthesis of Nicandrenones
Brian M. Stoltz; Taichi Kano; E. J. Corey; Journal of the American Chemical Society 122 (2000) 9044–9045; doi:10.1021/ja0024892

data_4116135
_publ_section_title
;
 Enantioselective Total Synthesis of Nicandrenones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9044
_journal_page_last               9045
_journal_paper_doi               10.1021/ja0024892
_journal_volume                  122
_journal_year                    2000
_chemical_formula_sum            'C30 H34 O3 Si'
_chemical_formula_weight         470.66
_chemical_melting_point          545(1)
_chemical_name_systematic
;
(2R,4aS,12aR)-8-Allyloxy-2-(dimethyl-phenyl-silanyl)-4a-methyl-2,3,5,6,12,12a-
hexahydro-1H,4aH-chrysene-4,11-dione
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.7297(6)
_cell_length_b                   37.2711(1)
_cell_length_c                   7.3366(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     5121.5(3)
_computing_cell_refinement       'SMART (Bruker, V4.050, 1995)'
_computing_data_collection       'ASTRO (Bruker, V4.050, 1995)'
_computing_data_reduction        'SAINT (Bruker, V5.A06, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998, ver 5.10)'
_computing_publication_material  'CIFTAB (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_method       '\w, 0.3 deg'
_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  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            14712
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.09
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.000000
_exptl_absorpt_correction_T_min  0.000000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       prism
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0609
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+1.9695P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1779
_reflns_number_gt                3717
_reflns_number_total             5895
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0024892.cif
_cod_data_source_block           goods
_cod_database_code               4116135