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_4025943
_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_absolute_configuration ad
_chemical_formula_sum            'C15 H20 Cl N O4'
_chemical_formula_weight         313.77
_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                 105.557(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6099(7)
_cell_length_b                   10.7142(7)
_cell_length_c                   13.7817(8)
_cell_measurement_reflns_used    1648
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      38.51
_cell_measurement_theta_min      4.70
_cell_volume                     1509.26(17)
_computing_cell_refinement
; 
  CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003) 
;
_computing_data_collection       'FRAMBO (BRUKER-NONIUS, 2003)'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_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 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'BRUKER GADDS D8 Discover'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9026
_diffrn_reflns_theta_full        59.98
_diffrn_reflns_theta_max         59.98
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    2.383
_exptl_absorpt_correction_T_max  0.9539
_exptl_absorpt_correction_T_min  0.7630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.311
_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   0.020(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         9031
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0537
_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^)+(0.0533P)^2^+0.4321P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1229
_reflns_number_gt                6635
_reflns_number_total             9031
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101638r_si_003.cif
_cod_data_source_block           twin5
_cod_database_code               4025943