Asymmetric Total Synthesis of Vindoline
Daisuke Kato; Yoshikazu Sasaki; Dale L. Boger; Journal of the American Chemical Society 132 (2010) 3685–3687; doi:10.1021/ja910695e

data_4102135
_publ_section_title
;
 Asymmetric Total Synthesis of Vindoline
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3685
_journal_page_last               3687
_journal_paper_doi               10.1021/ja910695e
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C30 H36 N2 O7'
_chemical_formula_weight         536.61
_chemical_name_systematic
; 
 ? 
;
_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                 95.00(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8185(16)
_cell_length_b                   8.3688(17)
_cell_length_c                   22.032(4)
_cell_measurement_reflns_used    3439
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.60
_cell_volume                     1436.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10610
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldricks, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4999
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.908
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0758
_refine_ls_shift/su_max          0.071
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1500P)^2^+0.6700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1988
_refine_ls_wR_factor_ref         0.2190
_reflns_number_gt                3787
_reflns_number_total             4999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja910695e_si_003.cif
_cod_data_source_block           ys628
_cod_database_code               4102135