Total Synthesis of (+)-Aspidospermidine: A New Strategy for the Enantiospecific Synthesis of Aspidosperma Alkaloids
Joseph P. Marino; Maria B. Rubio; Ganfeng Cao; Alfonso de Dios; Journal of the American Chemical Society 124 (2002) 13398–13399; doi:10.1021/ja026357f

data_4115267
_publ_section_title
;
 Total Synthesis of (+)-Aspidospermidine: A New Strategy for the
 Enantiospecific Synthesis of Aspidosperma Alkaloids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13398
_journal_page_last               13399
_journal_paper_doi               10.1021/ja026357f
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C33 H43 N O7 S'
_chemical_formula_weight         597.74
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.030(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.130(2)
_cell_length_b                   15.444(3)
_cell_length_c                   11.761(3)
_cell_measurement_reflns_used    4822
_cell_measurement_temperature    158(2)
_cell_measurement_theta_max      26.09
_cell_measurement_theta_min      2.31
_cell_volume                     1680.5(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      158(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            22085
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_type   SADABS
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(12)
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         6870
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0704
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0971P)^2^+1.0568P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1819
_refine_ls_wR_factor_ref         0.1908
_reflns_number_gt                5790
_reflns_number_total             6870
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja026357f-4_s2.cif
_cod_data_source_block           mbr330
_cod_original_cell_volume        1680.4(6)
_cod_database_code               4115267