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_4032394
_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_formula_moiety         'C17 H22 O4'
_chemical_formula_sum            'C17 H22 O4'
_chemical_formula_weight         290.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.142(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.1003(2)
_cell_length_b                   22.3395(4)
_cell_length_c                   13.9474(10)
_cell_measurement_reflns_used    16408
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      68.10
_cell_measurement_theta_min      6.70
_cell_volume                     3147.0(2)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21576
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.215
_diffrn_reflns_theta_min         6.650
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5393
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1136P)^2^+0.7651P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.2146
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3881
_reflns_number_total             5393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02921_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4032394
_shelx_estimated_absorpt_t_min   0.817
_shelx_estimated_absorpt_t_max   0.986
_shelxl_version_number           2013-2
_shelx_res_checksum              97788
_shelx_hkl_checksum              33651