Total Synthesis of Akuammiline Alkaloid (-)-Vincorine via Intramolecular Oxidative Coupling
Weiwei Zi; Weiqing Xie; Dawei Ma; Journal of the American Chemical Society 134 (2012) 9126–9129; doi:10.1021/ja303602f

data_4118030
_publ_section_title
;
 Total Synthesis of Akuammiline Alkaloid (-)-Vincorine via Intramolecular
 Oxidative Coupling
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9126
_journal_page_last               9129
_journal_paper_doi               10.1021/ja303602f
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C21 H26 N2 O3'
_chemical_formula_weight         354.44
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.313(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.844(5)
_cell_length_b                   13.658(7)
_cell_length_c                   13.066(7)
_cell_measurement_reflns_used    3084
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.924
_cell_measurement_theta_min      4.450
_cell_volume                     1826.3(16)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(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  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10560
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51991
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.211
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0859P)^2^+0.6890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1679
_reflns_number_gt                2668
_reflns_number_total             3588
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja303602f_si_002.cif
_cod_data_source_block           cd212142
_cod_original_cell_volume        1826.2(16)
_cod_database_code               4118030