Diastereoselective Total Synthesis of (±)-Basiliolide B and (±)-epi-8-Basiliolide B.
Liang, Xuefeng; Zhou, Liyan; Min, Long; Ye, Weijian; Bao, Wenli; Ma, Wenjing; Yang, Qianqian; Qiao, Fangfang; Zhang, Xinhao; Lee, Chi-Sing; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.6b02921

data_4032393
_publ_section_title
;
 Diastereoselective Total Synthesis of (+-)-Basiliolide B and
 (+-)-epi-8-Basiliolide B.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.6b02921
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C21 H24 O7'
_chemical_formula_sum            'C21 H24 O7'
_chemical_formula_weight         388.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   21.533(4)
_cell_length_b                   30.738(6)
_cell_length_c                   11.627(2)
_cell_measurement_reflns_used    5869
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.30
_cell_measurement_theta_min      2.31
_cell_volume                     7696(2)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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  0.0287
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16202
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.382
_diffrn_reflns_theta_min         2.098
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9571
_exptl_absorpt_correction_T_min  0.9311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SAINT ver 7.68b; BRUKER SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             3296
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.64
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1371 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4399
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+2.7466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.819
_reflns_number_gt                3655
_reflns_number_total             4399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02921_si_002.cif
_cod_data_source_block           zsulcs02
_cod_database_code               4032393
_shelx_estimated_absorpt_t_min   0.931
_shelx_estimated_absorpt_t_max   0.957
_shelxl_version_number           2013-4
_shelx_res_checksum              64247
_shelx_hkl_checksum              65723