Concise Formal Synthesis of (-)-Salinosporamide A (Marizomib) Using a Regio- and Stereoselective Epoxidation and Reductive Oxirane Ring-Opening Strategy
Taotao Ling; Barbara C. Potts; Venkat R. Macherla; Journal of Organic Chemistry 75 (2010) 3882–3885; doi:10.1021/jo100432g

data_4025451
_publ_section_title
;
 Concise Formal Synthesis of (-)-Salinosporamide A (Marizomib) Using a
 Regio- and Stereoselective Epoxidation and Reductive Oxirane Ring-Opening
 Strategy
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3882
_journal_page_last               3885
_journal_paper_doi               10.1021/jo100432g
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C15 H21 N O6'
_chemical_formula_weight         311.33
_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                 99.820(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.064(17)
_cell_length_b                   9.940(15)
_cell_length_c                   16.43(2)
_cell_measurement_reflns_used    8226
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.36
_cell_measurement_theta_min      2.40
_cell_volume                     1780(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0788
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6279
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9666
_exptl_absorpt_correction_T_min  0.9624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5048
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.2400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1340
_reflns_number_gt                4840
_reflns_number_total             5048
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100432g_si_002.cif
_cod_data_source_block           nereus19
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1780(5)
_cod_database_code               4025451