Total synthesis of (±)-tanshinol B, tanshinone I, and (±)-tanshindiol B and C.
Wang, Fan; Yang, Hong; Yu, Shujuan; Xue, Yu; Fan, Zhoulong; Liang, Gaolin; Geng, Meiyu; Zhang, Ao; Ding, Chunyong; Organic & biomolecular chemistry 16 (2018) 3376–3381; doi:10.1039/c8ob00567b

data_7157205
_publ_section_title
;
 Total synthesis of (+-)-tanshinol B, tanshinone I, and (+-)-tanshindiol B
 and C.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3376
_journal_page_last               3381
_journal_paper_doi               10.1039/c8ob00567b
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H16 O5, H2 O'
_chemical_formula_sum            'C18 H18 O6'
_chemical_formula_weight         330.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-02-26 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.992(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.3697(19)
_cell_length_b                   9.1064(7)
_cell_length_c                   6.6779(6)
_cell_measurement_reflns_used    4262
_cell_measurement_temperature    205
_cell_measurement_theta_max      72.869
_cell_measurement_theta_min      3.683
_cell_volume                     1459.5(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      205
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9163
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        63.978
_diffrn_reflns_theta_max         63.978
_diffrn_reflns_theta_min         3.683
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.947
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.6053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1278 before and 0.0515 after correction. The Ratio of minimum to maximum transmission is 0.8031. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Flack x determined using 937 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0660P)^2^+0.0890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0824
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                2227
_reflns_number_total             2262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00567b2.cif
_cod_data_source_block           cu_2017941-143-1_0m
_cod_database_code               7157205
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.887
_shelx_estimated_absorpt_t_min   0.777
_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 Free rotating group:
 O6(H6A)
2.b Ternary CH refined with riding coordinates:
 C10(H10)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C17(H17)
2.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C1(H1A,H1B,H1C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'