Total Synthesis of Alkaloid (\±)-G. B. 13 Using a Rh(I)-Catalyzed Ketone Hydroarylation and Late-Stage Pyridine Reduction
Kimberly K. Larson; Richmond Sarpong; Journal of the American Chemical Society 131 (2009) 13244–13245; doi:10.1021/ja9063487

data_4105055
_publ_section_title
;
 Total Synthesis of Alkaloid (\+-)-G. B. 13 Using a Rh(I)-Catalyzed Ketone
 Hydroarylation and Late-Stage Pyridine Reduction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13244
_journal_page_last               13245
_journal_paper_doi               10.1021/ja9063487
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C27 H29 Br N2 O6'
_chemical_formula_weight         557.43
_chemical_name_common            KLVII-033B
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.713(6)
_cell_angle_beta                 93.174(6)
_cell_angle_gamma                90.627(6)
_cell_formula_units_Z            2
_cell_length_a                   9.382(4)
_cell_length_b                   10.224(4)
_cell_length_c                   13.076(5)
_cell_measurement_reflns_used    8100
_cell_measurement_temperature    156(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2.5
_cell_volume                     1249.6(9)
_computing_cell_refinement       'Bruker-AXS SAINT v6.40'
_computing_data_collection       'Bruker-AXS SMART v5.631'
_computing_data_reduction        'Bruker-AXS SAINT v6.40'
_computing_molecular_graphics    'ORTEP-3 for Windows - Version 1.08'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       \w-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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8100
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_min         2.45
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.691
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.027(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         5915
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.170
_refine_ls_shift/su_mean         0.042
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.1023P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                4910
_reflns_number_total             5915
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9063487_si_002.cif
_cod_data_source_block           hlviis
_cod_original_cell_volume        1249.6(8)
_cod_database_code               4105055