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_4107192
_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_absolute_configuration unk
_chemical_formula_sum            'C29 H42.5 F3 N O5.5'
_chemical_formula_weight         550.14
_chemical_name_systematic
; 
 ? 
;
_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                84.552(7)
_cell_angle_beta                 88.780(10)
_cell_angle_gamma                62.157(6)
_cell_formula_units_Z            2
_cell_length_a                   10.083(6)
_cell_length_b                   10.455(5)
_cell_length_c                   15.230(7)
_cell_measurement_reflns_used    3939
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.32
_cell_volume                     1412.7(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_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 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega 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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.1174
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15154
_diffrn_reflns_theta_full        27.68
_diffrn_reflns_theta_max         27.68
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             589
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.4(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     700
_refine_ls_number_reflns         11763
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1595
_refine_ls_R_factor_gt           0.0957
_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^)+(0.1582P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2300
_refine_ls_wR_factor_ref         0.2753
_reflns_number_gt                6505
_reflns_number_total             11763
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja207385y_si_004.cif
_cod_data_source_block           p1m
_cod_original_cell_volume        1412.7(12)
_cod_original_formula_sum        'C29 H42.50 F3 N O5.50'
_cod_database_code               4107192