Total Synthesis, Relay Synthesis, and Structural Confirmation of the C18-Norditerpenoid Alkaloid Neofinaconitine
Yuan Shi; Jeremy T. Wilmot; Lars Ulrik Nordstrøm; Derek S. Tan; David Y. Gin; Journal of the American Chemical Society 135 (2013) 14313–14320; doi:10.1021/ja4064958

data_4120844
_publ_section_title
;
 Total Synthesis, Relay Synthesis, and Structural Confirmation of the
 C18-Norditerpenoid Alkaloid Neofinaconitine
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14313
_journal_page_last               14320
_journal_paper_doi               10.1021/ja4064958
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C24 H31 Br2 N O5'
_chemical_formula_weight         573.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 108.73(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.855(3)
_cell_length_b                   11.319(2)
_cell_length_c                   17.342(4)
_cell_measurement_reflns_used    5479
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.98
_cell_volume                     2389.7(10)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_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  0.0627
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16723
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    3.428
_exptl_absorpt_correction_T_max  0.7256
_exptl_absorpt_correction_T_min  0.2791
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   numerical
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0278P)^2^+3.6133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                4217
_reflns_number_total             5479
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4064958_si_004.cif
_cod_data_source_block           x1722l
_cod_database_code               4120844