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_4120843
_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            'C44 H69 N O7 Si2'
_chemical_formula_weight         780.18
_space_group_IT_number           2
_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                73.44(3)
_cell_angle_beta                 88.29(3)
_cell_angle_gamma                75.53(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7140(15)
_cell_length_b                   15.131(3)
_cell_length_c                   20.518(4)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.96
_cell_volume                     2220.5(9)
_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 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.1010
_diffrn_reflns_av_sigmaI/netI    0.1247
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25341
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9555
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   numerical
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.431
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         9925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.2446
_refine_ls_R_factor_gt           0.1886
_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^)+(0.0923P)^2^+38.5326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4121
_refine_ls_wR_factor_ref         0.4428
_reflns_number_gt                6544
_reflns_number_total             9925
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4064958_si_003.cif
_cod_data_source_block           x1658l
_cod_original_cell_volume        2220.5(8)
_cod_database_code               4120843