A Benzyne Insertion Approach to Hetisine-Type Diterpenoid Alkaloids: Synthesis of Cossonidine (Davisine).
Kou, Kevin G. M.; Pflueger, Jason J.; Kiho, Toshihiro; Morrill, Louis C.; Fisher, Ethan L.; Clagg, Kyle; Lebold, Terry P.; Kisunzu, Jessica K.; Sarpong, Richmond; Journal of the American Chemical Society 140 (2018) 8105–8109; doi:10.1021/jacs.8b05043

data_4132594
_publ_section_title
;
 A Benzyne Insertion Approach to Hetisine-Type Diterpenoid Alkaloids:
 Synthesis of Cossonidine (Davisine).
;
_journal_issue                   26
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8105
_journal_page_last               8109
_journal_paper_doi               10.1021/jacs.8b05043
_journal_volume                  140
_journal_year                    2018
_chemical_formula_sum            'C27 H39 Br O6 Si'
_chemical_formula_weight         567.58
_chemical_name_common            LCM1/Acid
_chemical_name_systematic        sarpong103
_space_group.centring_type       primitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                75.572(2)
_cell_angle_beta                 76.098(2)
_cell_angle_gamma                66.854(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0108(4)
_cell_length_b                   10.7633(4)
_cell_length_c                   16.4963(6)
_cell_measurement_reflns_used    9625
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      4.54
_cell_volume                     1406.42(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_refln_scan_rate          5
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            64020
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.500
_diffrn_reflns_theta_min         2.802
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    2.709
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       rod
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.946
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0577P)^2^+1.1940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4787
_reflns_number_total             5060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05043_si_002.cif
_cod_data_source_block           sarpong103
_cod_database_code               4132594
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.948
_shelx_res_checksum              34835
_shelx_hkl_checksum              4034