Asymmetric Total Synthesis of Vindorosine, Vindoline, and Key Vinblastine Analogues
Yoshikazu Sasaki; Daisuke Kato; Dale L. Boger; Journal of the American Chemical Society 132 (2010) 13533–13544; doi:10.1021/ja106284s

data_4103120
_publ_section_title
;
 Asymmetric Total Synthesis of Vindorosine, Vindoline, and Key Vinblastine
 Analogues
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13533
_journal_page_last               13544
_journal_paper_doi               10.1021/ja106284s
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C24 H31 Cl N2 O5'
_chemical_formula_weight         462.96
_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            8
_cell_length_a                   15.515(3)
_cell_length_b                   16.884(3)
_cell_length_c                   17.999(4)
_cell_measurement_reflns_used    6453
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.41
_cell_volume                     4714.9(16)
_computing_cell_refinement       'Bruker SAINT+'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34770
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.65
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.9556
_exptl_absorpt_correction_T_min  0.9371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (SHeldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block-shaped
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.161
_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   0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     587
_refine_ls_number_reflns         8304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.100
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+0.3600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                7154
_reflns_number_total             8304
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106284s_si_005.cif
_cod_data_source_block           yaki
_cod_database_code               4103120