Bioinspired Total Synthesis and Human Proteasome Inhibitory Activity of (-)-Salinosporamide A, (-)-Homosalinosporamide A, and Derivatives Obtained via Organonucleophile Promoted Bis-cyclizations
Henry Nguyen; Gil Ma; Tatiana Gladysheva; Trisha Fremgen; Daniel Romo; Journal of Organic Chemistry 76 (2011) 2–12; doi:10.1021/jo101638r

data_4025942
_publ_section_title
;
 Bioinspired Total Synthesis and Human Proteasome Inhibitory Activity of
 (-)-Salinosporamide A, (-)-Homosalinosporamide A, and Derivatives
 Obtained via Organonucleophile Promoted Bis-cyclizations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2
_journal_page_last               12
_journal_paper_doi               10.1021/jo101638r
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C15 H16 Cl N O4'
_chemical_formula_weight         309.74
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.007(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.516(3)
_cell_length_b                   11.0290(13)
_cell_length_c                   16.725(2)
_cell_measurement_reflns_used    947
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      54.56
_cell_measurement_theta_min      3.85
_cell_volume                     2861.6(7)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'MWPC area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1021
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            48543
_diffrn_reflns_theta_full        59.98
_diffrn_reflns_theta_max         59.98
_diffrn_reflns_theta_min         3.85
_exptl_absorpt_coefficient_mu    2.513
_exptl_absorpt_correction_T_max  0.9515
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'colorless '
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       'plate     '
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; calc                                                                         
 [0.00000+1.00000exp(1.70(sin\q/\l)^2^)]/                                      
   [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0671P)^2^+0.0000sin\q/\l]                  
 where P = 0.33333Fo^2^ + 0.66667Fc^2^                                         
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                2714
_reflns_number_total             4192
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101638r_si_002.cif
_cod_data_source_block           dr69
_cod_original_cell_volume        2861.5(7)
_cod_database_code               4025942