Total Synthesis of (-)-Spirotryprostatin B: Synthesis and Related Studies
Christiane Marti; Erick M. Carreira; Journal of the American Chemical Society 127 (2005) 11505–11515; doi:10.1021/ja0518880

data_4111863
_publ_section_title
;
 Total Synthesis of (-)-Spirotryprostatin B: Synthesis and Related Studies
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11505
_journal_page_last               11515
_journal_paper_doi               10.1021/ja0518880
_journal_volume                  127
_journal_year                    2005
_chemical_formula_moiety         'C27 H35 N3 O6 * C D CL3'
_chemical_formula_sum            'C28 H36 Cl3 N3 O6'
_chemical_formula_weight         616.95
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9350(10)
_cell_length_b                   13.870(2)
_cell_length_c                   25.228(7)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      21.90
_cell_measurement_theta_min      18.90
_cell_volume                     3126.5(10)
_computing_cell_refinement       'CAD4 VMS-software (Nonius, 1989)'
_computing_data_collection       'CAD4 VMS-software (Nonius, 1989)'
_computing_data_reduction        'MOLEN VMS-software (Nonius, 1990)'
_computing_molecular_graphics    'ORTEP (Johnson,1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,1994)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'NONIUS CAD4'
_diffrn_measurement_method       \q/\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3368
_diffrn_reflns_theta_full        69.98
_diffrn_reflns_theta_max         69.98
_diffrn_reflns_theta_min         3.50
_diffrn_standards_decay_%        3.100
_diffrn_standards_interval_time  '167 min.'
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    3.020
_exptl_absorpt_correction_T_max  0.5834
_exptl_absorpt_correction_T_min  0.4644
_exptl_absorpt_correction_type   'no correction'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       'Cut fragment'
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    'H-atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         3340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0608
_refine_ls_shift/su_max          0.314
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.1902
_reflns_number_gt                2945
_reflns_number_total             3340
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0518880si20050405_034309.cif
_cod_data_source_block           meyers2
_cod_database_code               4111863
_refine_ls_weigthing_details
'w=1/[\s^2^(Fo^2^)+(0.1193P)^2^+1.8272P] where P=(Fo^2^+2Fc^2^)/3'