A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans-ozic acid.
Li, Fu-Zhuo; Li, Shuang; Zhang, Peng-Peng; Huang, Zhi-Hui; Zhang, Wei-Bin; Gong, Jianxian; Yang, Zhen; Chemical communications (Cambridge, England) 52 (2016) 12426–12429; doi:10.1039/c6cc06794h

data_7125099
_publ_section_title
;
 A chiral pool approach for asymmetric syntheses of (-)-antrocin,
 (+)-asperolide C, and (-)-trans-ozic acid.
;
_journal_issue                   84
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12426
_journal_page_last               12429
_journal_paper_doi               10.1039/c6cc06794h
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H24 O3'
_chemical_formula_sum            'C15 H24 O3'
_chemical_formula_weight         252.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-08-30 deposited with the CCDC.
2016-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.735(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.97920(10)
_cell_length_b                   6.68480(10)
_cell_length_c                   10.2099(7)
_cell_measurement_reflns_used    8662
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.10
_cell_measurement_theta_min      6.60
_cell_volume                     676.39(5)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9042
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_min         6.602
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       prism
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 817 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2363
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0645P)^2^+0.0616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1346
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                2096
_reflns_number_total             2363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc06794h2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7125099
_shelxl_version_number           2014-3
_shelx_res_checksum              18158