Ivorenolide A, an Unprecedented Immunosuppressive Macrolide from Khaya ivorensis: Structural Elucidation and Bioinspired Total Synthesis
Bo Zhang; Yao Wang; Sheng-Ping Yang; Yu Zhou; Wen-Bin Wu; Wei Tang; Jian-Ping Zuo; Ying Li; Jian-Min Yue; Journal of the American Chemical Society 134 (2012) 20605–20608; doi:10.1021/ja310482z

data_4119054
_publ_section_title
;
 Ivorenolide A, an Unprecedented Immunosuppressive Macrolide from Khaya
 ivorensis: Structural Elucidation and Bioinspired Total Synthesis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20605
_journal_page_last               20608
_journal_paper_doi               10.1021/ja310482z
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_sum            'C18 H24 O5'
_chemical_formula_weight         320.37
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9507(4)
_cell_length_b                   7.5613(7)
_cell_length_c                   45.518(4)
_cell_measurement_reflns_used    4194
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.865
_cell_measurement_theta_min      5.370
_cell_volume                     1703.9(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_number            10030
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7837
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.369
_exptl_crystal_size_min          0.314
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2235
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0650P)^2^+0.1308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                2043
_reflns_number_total             2235
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja310482z_si_001.cif
_cod_data_source_block           cd28223
_cod_database_code               4119054