Enantioselective Total Syntheses of Omuralide, 7-epi-Omuralide, and (+)-Lactacystin
Christopher J. Hayes; Alexandra E. Sherlock; Martin P. Green; Claire Wilson; Alexander J. Blake; Matthew D. Selby; Jeremy C. Prodger; Journal of Organic Chemistry 73 (2008) 2041–2051; doi:10.1021/jo7027695

data_4023354
_publ_section_title
;
 Enantioselective Total Syntheses of Omuralide, 7-epi-Omuralide,
 and (+)-Lactacystin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2041
_journal_page_last               2051
_journal_paper_doi               10.1021/jo7027695
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H22 Br N O2'
_chemical_formula_weight         352.27
_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,  sp2 bound Me from difmap'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.117(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.947(2)
_cell_length_b                   5.9259(8)
_cell_length_c                   12.668(2)
_cell_measurement_reflns_used    2756
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      3.3
_cell_volume                     861.6(2)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2002)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL v6.12 (Bruker, 2'
_computing_publication_material  'SHELXL-97; PLATON (Spek, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.056
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7623
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.76
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.389
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker SHELXTL v6.12'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0566P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                3143
_reflns_number_total             3856
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo7027695-File001.cif
_cod_data_source_block           brenep
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023354