A Short and Efficient Synthesis of (-)-7-Methylomuralide, a Potent Proteasome Inhibitor
Ryan A. Shenvi; E. J. Corey; Journal of the American Chemical Society 131 (2009) 5746–5747; doi:10.1021/ja901400q

data_4104256
_publ_section_title
;
 A Short and Efficient Synthesis of (-)-7-Methylomuralide, a Potent
 Proteasome Inhibitor
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5746
_journal_page_last               5747
_journal_paper_doi               10.1021/ja901400q
_journal_volume                  131
_journal_year                    2009
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac          'C17 H27 N O7'
_chemical_formula_moiety         'C17 H27 N O7'
_chemical_formula_structural     'C17 H27 N O7'
_chemical_formula_sum            'C17 H27 N O7'
_chemical_formula_weight         357.40
_chemical_name_common            RAS-2-233
_chemical_name_systematic
; 
Methyl 2-(1-(<i>tert</i>-butoxycarbonyloxy)-2-methylpropyl)-4,4-
dimethyl-3,5-dioxopyrrolidine-2-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 123.631(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1872(2)
_cell_length_b                   10.3016(2)
_cell_length_c                   18.9412(4)
_cell_measurement_reflns_used    7781
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.23
_cell_volume                     1979.99(7)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SHELXTL v6.12 (Bruker AXS, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       '\w scans, 1533 0.5\% rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31517
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.331
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.132
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0627
_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
'w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+0.3578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                4277
_reflns_number_total             5782
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja901400q_si_002.cif
_cod_data_source_block           ejc156
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4104256