Development and Scope of the Arene-Fused Domino Michael/Mannich Reaction: Application to the Total Syntheses of Aspidosperma Alkaloids (-)-Aspidospermidine, (-)-Tabersonine, and (-)-Vincadifformine.
Zhao, Senzhi; Andrade, Rodrigo B.; The Journal of organic chemistry 82 (2017) 521–531; doi:10.1021/acs.joc.6b02551

data_4032210
_publ_section_title
;
 Development and Scope of the Arene-Fused Domino Michael/Mannich Reaction:
 Application to the Total Syntheses of Aspidosperma Alkaloids
 (-)-Aspidospermidine, (-)-Tabersonine, and (-)-Vincadifformine.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              521
_journal_page_last               531
_journal_paper_doi               10.1021/acs.joc.6b02551
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H27 N2 O5 S2'
_chemical_formula_sum            'C25 H27 N2 O5 S2'
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_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
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_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
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_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.865(7)
_cell_length_b                   24.087(10)
_cell_length_c                   6.115(3)
_cell_measurement_reflns_used    4100
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.322
_cell_measurement_theta_min      2.566
_cell_volume                     2484.1(19)
_computing_cell_refinement       'SAINT (Bruker AXS)'
_computing_data_collection       'COSMO (Bruker AXS)'
_computing_data_reduction        'SADABS (Bruker AXS)'
_computing_molecular_graphics    'Mercury (CCDC)'
_computing_publication_material  'APEX2 (Bruker AXS)'
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_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
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_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Kappa APEX II DUO'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.988
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_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
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_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.863
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_diffrn_source                   'sealed tube'
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_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7637
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;

    11034 Corrected reflections written to file
 Estimated minimum and maximum transmission:  0.7637  1.0000
 The ratio of these values is more reliable than their absolute values!
 Additional spherical absorption correction applied with mu*r =  0.0000
 Lambda/2 correction factor = 0.0015
;
_exptl_crystal_colour            colorless
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_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 1527 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         5677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.9848P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                4354
_reflns_number_total             5677
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02551_si_002.cif
_cod_data_source_block           final
_cod_original_cell_volume        2484.1(18)
_cod_database_code               4032210
_shelx_estimated_absorpt_t_min   0.859
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2013-2
_shelx_res_checksum              12599
_shelx_hkl_checksum              76084