Total Synthesis of Prostratin, a Bioactive Tigliane Diterpenoid: Access to Multi-Stereocenter Cyclohexanes from a Phenol.
Tong, Guanghu; Ding, Zhengwei; Liu, Zhi; Ding, You-Song; Xu, Liang; Zhang, Hailong; Li, Pengfei; The Journal of organic chemistry 85 (2020) 4813–4837; doi:10.1021/acs.joc.0c00022

data_4038089
_publ_section_title
;
 Total Synthesis of Prostratin, a Bioactive Tigliane Diterpenoid: Access
 to Multi-Stereocenter Cyclohexanes from a Phenol.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4813
_journal_page_last               4837
_journal_paper_doi               10.1021/acs.joc.0c00022
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C25 H40 O5'
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_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
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_cell_angle_gamma                90
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_cell_length_a                   11.6702(2)
_cell_length_b                   18.6897(3)
_cell_length_c                   21.5803(4)
_cell_measurement_reflns_used    11506
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.2610
_cell_measurement_theta_min      4.0740
_cell_volume                     4706.93(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
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_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
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_diffrn_reflns_theta_max         74.479
_diffrn_reflns_theta_min         4.097
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57815
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLESS
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_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1840
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4710
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_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0421
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_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+1.5144P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4316
_reflns_number_total             4710
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00022_si_002.cif
_cod_data_source_block           tgh9127p1
_cod_depositor_comments
;
Adding full bibliography for 4038084--4038097.cif.

2020-10-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C20 H32 O4'
_cod_original_formula_units_Z    10
_cod_original_formula_weight     336.45
_cod_database_code               4038089
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              606
_shelx_hkl_checksum              21861