A1,3-strain enabled retention of chirality during bis-cyclization of β-ketoamides: total synthesis of (−)-salinosporamide A and (−)-homosalinosporamide A
Nguyen, Henry; Ma, Gil; Romo, Daniel; Chemical Communications 46 (2010) 4803–4805; doi:10.1039/c0cc00607f

data_7111723
_publ_section_title
;
 A1,3-strain enabled retention of chirality during bis-cyclization of
 \b-ketoamides: total synthesis of (&#x2212;)-salinosporamide A and
 (&#x2212;)-homosalinosporamide A
;
_journal_issue                   26
_journal_name_full               'Chemical Communications'
_journal_page_first              4803
_journal_page_last               4805
_journal_paper_doi               10.1039/c0cc00607f
_journal_volume                  46
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_formula_sum            'C64 H87 Cl4 N4 O16'
_chemical_formula_weight         1310.18
_chemical_name_systematic
;
?
;
_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                 93.571(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.694(3)
_cell_length_b                   25.624(9)
_cell_length_c                   13.118(4)
_cell_measurement_reflns_used    305
_cell_measurement_temperature    383(2)
_cell_measurement_theta_max      30.19
_cell_measurement_theta_min      3.45
_cell_volume                     3252.2(18)
_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      383(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.2299
_diffrn_reflns_av_sigmaI/netI    0.2850
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24861
_diffrn_reflns_theta_full        59.99
_diffrn_reflns_theta_max         59.99
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    2.234
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.8776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'colorless '
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'needle '
_exptl_crystal_F_000             1390
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     832
_refine_ls_number_reflns         9114
_refine_ls_number_restraints     649
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1842
_refine_ls_R_factor_gt           0.0821
_refine_ls_shift/su_max          0.133
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; calc
[0.00000+1.00000exp(1.80(sin\q/\l)^2^)]/
[\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0100P)^2^+0.0000sin\q/\l]
where P = 0.33333Fo^2^ + 0.66667Fc^2^
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1448
_reflns_number_gt                3455
_reflns_number_total             9114
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC00607Fsup1.cif
_cod_data_source_block           dr72
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7111723