Total Synthesis of (-)-Batrachotoxinin A: A Local-Desymmetrization Approach.
Guo, Yinliang; Guo, Zhixian; Lu, Jia-Tian; Fang, Runting; Chen, Si-Cong; Luo, Tuoping; Journal of the American Chemical Society 142 (2020) 3675–3679; doi:10.1021/jacs.9b12882

data_4134191
_publ_section_title
;
 Total Synthesis of (-)-Batrachotoxinin A: A Local-Desymmetrization
 Approach.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3675
_journal_page_last               3679
_journal_paper_doi               10.1021/jacs.9b12882
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H28 O5'
_chemical_formula_weight         372.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.1237(3)
_cell_length_b                   12.3532(3)
_cell_length_c                   20.8073(4)
_cell_measurement_reflns_used    21682
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      74.8690
_cell_measurement_theta_min      3.5300
_cell_volume                     3630.31(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            55865
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.091
_diffrn_reflns_theta_min         3.578
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2919 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         7428
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0803P)^2^+0.4618P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1188
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                6611
_reflns_number_total             7428
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12882_si_005.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 4134185--4134193.cif.'
_cod_database_code               4134191
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              35237
_shelx_hkl_checksum              24300