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_4038090
_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_absolute_configuration unk
_chemical_formula_moiety         'C25 H40 O6'
_chemical_formula_sum            'C25 H40 O6'
_chemical_formula_weight         436.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-08-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6740(10)
_cell_length_b                   11.5004(13)
_cell_length_c                   23.904(3)
_cell_measurement_reflns_used    3139
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.77
_cell_measurement_theta_min      2.46
_cell_volume                     2384.5(5)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11993
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        24.804
_diffrn_reflns_theta_max         24.804
_diffrn_reflns_theta_min         1.704
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 968 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.676
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.676
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0383
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1138
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2981
_reflns_number_total             4043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00022_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4038084--4038097.cif.'
_cod_database_code               4038090
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5A), C17(H17), C6(H6), C15(H15), C8(H8), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C7(H7A,H7B), C10(H10A,H10B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21)
2.d X=CH2 refined with riding coordinates:
 C22(H22A,H22B), C13(H13A,H13B)
2.e Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C11(H11A,H11B,H11C), C1(H1A,H1B,
 H1C), C25(H25A,H25B,H25C), C3(H3A,H3B,H3C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O5(H5)
;
_shelx_res_checksum              26246
_shelx_hkl_checksum              99946
_olex2_submission_special_instructions 'No special instructions were received'