Diastereoselective synthesis of fused lactone-pyrrolidinones; application to a formal synthesis of (-)-salinosporamide a.
Logan, Angus W. J.; Sprague, Simon J.; Foster, Robert W.; Marx, Léo B; Garzya, Vincenzo; Hallside, Michal S.; Thompson, Amber L.; Burton, Jonathan W.; Organic letters 16 (2014) 4078–4081; doi:10.1021/ol501662t

data_1517237
_publ_section_title
;
 Diastereoselective synthesis of fused lactone-pyrrolidinones; application
 to a formal synthesis of (-)-salinosporamide a.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4078
_journal_page_last               4081
_journal_paper_doi               10.1021/ol501662t
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C26 H35 N1 O6'
_chemical_formula_sum            'C26 H35 N O6'
_chemical_formula_weight         457.57
_chemical_melting_point          ?
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2012-09-24
_audit_creation_method           CRYSTALS_ver_14.52
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2769(1)
_cell_length_b                   19.0465(2)
_cell_length_c                   20.3494(4)
_cell_measurement_reflns_used    14442
_cell_measurement_temperature    100
_cell_measurement_theta_max      32
_cell_measurement_theta_min      2
_cell_volume                     2432.83(7)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2009)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Rigaku Saturn724+'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            32517
_diffrn_reflns_theta_full        25.199
_diffrn_reflns_theta_max         31.898
_diffrn_reflns_theta_min         2.073
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9344
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4704
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.0005171
_refine_ls_shift/su_mean         0.0000523
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.252E+04 0.418E+04 0.269E+04 0.120E+04 328. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0999
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0999
_reflns_limit_h_max              9
_reflns_limit_h_min              0
_reflns_limit_k_max              29
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                4416
_reflns_number_total             4716
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.70
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0425
_oxford_refine_ls_scale          8.8(2)
_oxford_reflns_number_all        4704
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title DIA0174
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  62,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 143,X'S) H   ( 142,X'S) 
RIDE C   (  16,X'S) H   ( 162,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 192,X'S) H   ( 191,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 243,X'S) H   ( 242,X'S) 
RIDE C   (  25,X'S) H   ( 252,X'S) H   ( 251,X'S) H   ( 253,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 263,X'S) H   ( 261,X'S) 
RIDE C   (  31,X'S) H   ( 313,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 323,X'S) H   ( 322,X'S) 
RIDE C   (  33,X'S) H   ( 332,X'S) H   ( 331,X'S) H   ( 333,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            ol501662t_si_002.cif
_cod_data_source_block           18
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_atom_sites_solution_primary'
value 'Other' changed to 'other' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1517236--1517237.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C26 H35 N1 O6'
_cod_database_code               1517237