Total Synthesis of the Spirocyclic Imine Marine Toxin (-)-Gymnodimine and an Unnatural C4-Epimer
Ke Kong; Ziad Moussa; Changsuk Lee; Daniel Romo; Journal of the American Chemical Society 133 (2011) 19844–19856; doi:10.1021/ja207385y

data_4107190
_publ_section_title
;
 Total Synthesis of the Spirocyclic Imine Marine Toxin (-)-Gymnodimine and
 an Unnatural C4-Epimer
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19844
_journal_page_last               19856
_journal_paper_doi               10.1021/ja207385y
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C27 H39 N O4 S Si'
_chemical_formula_weight         501.74
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 103.037(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.3818(6)
_cell_length_b                   6.4515(3)
_cell_length_c                   15.0178(6)
_cell_measurement_reflns_used    6421
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      60.62
_cell_measurement_theta_min      3.02
_cell_volume                     1357.50(10)
_computing_cell_refinement       'CELL_NOW(Sheldrick, 2003), Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_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      110(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Multi-wire area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10860
_diffrn_reflns_theta_full        59.20
_diffrn_reflns_theta_max         59.20
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    1.736
_exptl_absorpt_correction_T_max  0.8881
_exptl_absorpt_correction_T_min  0.4773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      0
_exptl_crystal_description       Needle
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3305
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0711
_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^)+(0.1652P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1743
_refine_ls_wR_factor_ref         0.1900
_reflns_number_gt                3126
_reflns_number_total             3305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja207385y_si_002.cif
_cod_data_source_block           kkgnm
_cod_database_code               4107190