Total Synthesis of the NF-κB Inhibitor (-)-Cycloepoxydon: Utilization of Tartrate-Mediated Nucleophilic Epoxidation
Chaomin Li; Emily A. Pace; Mei-Chih Liang; Emil Lobkovsky; Thomas D. Gilmore; John A. Porco; Journal of the American Chemical Society 123 (2001) 11308–11309; doi:10.1021/ja0169769

data_4115782
_publ_section_title
;
 Total Synthesis of the NF-\kB Inhibitor (-)-Cycloepoxydon: Utilization of
 Tartrate-Mediated Nucleophilic Epoxidation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11308
_journal_page_last               11309
_journal_paper_doi               10.1021/ja0169769
_journal_volume                  123
_journal_year                    2001
_chemical_formula_sum            'C12 H16 O5'
_chemical_formula_weight         240.25
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.890(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.1459(10)
_cell_length_b                   4.5094(7)
_cell_length_c                   17.904(3)
_cell_measurement_temperature    173(2)
_cell_volume                     576.20(15)
_computing_cell_refinement       SAINT+
_computing_data_collection       SMART
_computing_data_reduction        SAINT+
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker 1K CCD'
_diffrn_measurement_method       '0.3 deg. omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2626
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_correction_T_min  0.4849
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       'flat needle'
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         1540
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.306
_refine_ls_shift/su_mean         0.030
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.1573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                1283
_reflns_number_total             1540
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0169769_s3.cif
_cod_data_source_block           porco4
_cod_original_cell_volume        576.22(14)
_cod_database_code               4115782