Efficient Syntheses of (-)-Crinine and (-)-Aspidospermidine, and Formal Synthesis of (-)-Minfiensine by Enantioselective Intramolecular Dearomative Cyclization
Tang, Wenjun; Du, Kang; Yang, He; Guo, Pan; Feng, Liang; Xu, Guangqing; Zhou, Qing-Hai; Chung, Lung Wa; Chem. Sci.  (2017) –; doi:10.1039/C7SC01859B

data_1546442
_publ_section_title
;
 Efficient Syntheses of (-)-Crinine and (-)-Aspidospermidine, and Formal
 Synthesis of (-)-Minfiensine by Enantioselective Intramolecular
 Dearomative Cyclization
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC01859B
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H35 N4 O4 P'
_chemical_formula_sum            'C23 H35 N4 O4 P'
_chemical_formula_weight         462.52
_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
_audit_update_record
;
2017-03-10 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.25(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.632(2)
_cell_length_b                   10.796(2)
_cell_length_c                   20.144(4)
_cell_measurement_reflns_used    9831
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.44
_cell_measurement_theta_min      3.80
_cell_volume                     2527.7(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            36018
_diffrn_reflns_theta_full        68.44
_diffrn_reflns_theta_max         68.44
_diffrn_reflns_theta_min         3.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.247
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.030(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         9086
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.7297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                8404
_reflns_number_total             9086
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7sc01859b2.cif
_cod_data_source_block           434
_cod_original_cell_volume        2527.6(9)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1546442