Enantioselective Synthesis of Protected Nitrocyclohexitols with Five Stereocenters. Total Synthesis of (+)-Pancratistatin
Fernando Cagide-Fagín; Olaia Nieto-García; Hugo Lago-Santomé; Ricardo Alonso; Journal of Organic Chemistry 77 (2012) 11377–11382; doi:10.1021/jo3022567

data_4027798
_publ_section_title
;
 Enantioselective Synthesis of Protected Nitrocyclohexitols with Five
 Stereocenters. Total Synthesis of (+)-Pancratistatin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11377
_journal_page_last               11382
_journal_paper_doi               10.1021/jo3022567
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H18 Br1 N1 O8'
_chemical_formula_sum            'C20 H18 Br N O8'
_chemical_formula_weight         480.26
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2007-02-27T17:21:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.011(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8847(3)
_cell_length_b                   8.9681(3)
_cell_length_c                   14.7329(5)
_cell_measurement_reflns_used    1959
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.72
_cell_measurement_theta_min      2.64
_cell_measurement_wavelength     0.71073
_cell_volume                     1018.97(6)
_computing_cell_refinement       'APPEX2 (BRUKER AXS, 2005)'
_computing_data_collection       'APPEX2 (BRUKER AXS, 2005)'
_computing_data_reduction        'APPEX2 (BRUKER AXS, 2005)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97  (Giacovazzo et all, 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'BRUKER APPEX-II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            52665
_diffrn_reflns_theta_full        32.02
_diffrn_reflns_theta_max         32.02
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    2.065
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.613
_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   0.001(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.233
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         7087
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.045
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0282P)^2^+0.0683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.069
_refine_ls_wR_factor_ref         0.0711
_reflns_number_gt                6017
_reflns_number_total             7087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3022567_si_002.cif
_cod_data_source_block           ra02ky1n
_cod_database_code               4027798