Stereospecific Total Syntheses of Proteasome Inhibitors Omuralide and Lactacystin
Wenxin Gu; Richard B. Silverman; Journal of Organic Chemistry 76 (2011) 8287–8293; doi:10.1021/jo201453x

data_4026646
_publ_section_title
;
 Stereospecific Total Syntheses of Proteasome Inhibitors Omuralide and
 Lactacystin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8287
_journal_page_last               8293
_journal_paper_doi               10.1021/jo201453x
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_sum            'C20 H27 N O7'
_chemical_formula_weight         393.43
_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                 110.073(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.7688(10)
_cell_length_b                   9.7160(11)
_cell_length_c                   12.4390(14)
_cell_measurement_reflns_used    4304
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      2.47
_cell_volume                     995.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      153(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9288
_diffrn_reflns_theta_full        28.89
_diffrn_reflns_theta_max         28.89
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'face indexed'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4649
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0433P)^2^+0.1537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                3812
_reflns_number_total             4649
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201453x_si_002.cif
_cod_data_source_block           s66v
_cod_database_code               4026646