A Synthetic Approach to Ervatamine-Silicine Alkaloids. Enantioselective Total Synthesis of (-)-16-Episilicine
Mercedes Amat; Núria Llor; Begoña Checa; Elies Molins; Joan Bosch; Journal of Organic Chemistry 75 (2010) 178–189; doi:10.1021/jo902346j

data_4025143
_publ_section_title
;
 A Synthetic Approach to Ervatamine-Silicine Alkaloids. Enantioselective
 Total Synthesis of (-)-16-Episilicine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              178
_journal_page_last               189
_journal_paper_doi               10.1021/jo902346j
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C34 H34 N2 O4 S, C H4 O'
_chemical_formula_sum            'C35 H38 N2 O5 S'
_chemical_formula_weight         598.73
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2009-06-25T19:30:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.66(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2040(18)
_cell_length_b                   14.1890(18)
_cell_length_c                   11.795(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      6.5
_cell_measurement_wavelength     0.71073
_cell_volume                     1535.3(5)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.004169
_diffrn_orient_matrix_UB_12      -0.009153
_diffrn_orient_matrix_UB_13      -0.084246
_diffrn_orient_matrix_UB_21      0.003391
_diffrn_orient_matrix_UB_22      0.069821
_diffrn_orient_matrix_UB_23      -0.01091
_diffrn_orient_matrix_UB_31      0.108893
_diffrn_orient_matrix_UB_32      -0.002529
_diffrn_orient_matrix_UB_33      0.003967
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.1063
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2793
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.73
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.9702
_exptl_absorpt_correction_T_min  0.9089
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         2793
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1446
_reflns_number_gt                1499
_reflns_number_total             2793
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902346j_si_003.cif
_cod_data_source_block           jb71
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025143