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_4102134
_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            'C31 H37.75 N2 O7'
_chemical_formula_weight         550.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            16
_cell_length_a                   18.014(4)
_cell_length_b                   24.694(5)
_cell_length_c                   26.113(5)
_cell_measurement_reflns_used    4887
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.90
_cell_measurement_theta_min      2.39
_cell_volume                     11616(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1094
_diffrn_reflns_av_sigmaI/netI    0.0929
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            58290
_diffrn_reflns_theta_full        20.84
_diffrn_reflns_theta_max         20.84
_diffrn_reflns_theta_min         1.37
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate-like
_exptl_crystal_F_000             4700
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.302
_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   -0.5(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1349
_refine_ls_number_reflns         12214
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1520
_refine_ls_R_factor_gt           0.0784
_refine_ls_shift/su_max          0.157
_refine_ls_shift/su_mean         0.021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1919
_refine_ls_wR_factor_ref         0.2458
_reflns_number_gt                6715
_reflns_number_total             12214
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja910695e_si_002.cif
_cod_data_source_block           ysan
_cod_database_code               4102134