Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B
Lu, Xiao-Long; Qiu, Yuanyou; Yang, Baochao; He, Haibing; Gao, Shuanhu; Chemical Science 12 (2021) 4747–4752; doi:10.1039/D0SC07089K

data_1560504
_publ_section_title
;
 Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A
 and B
;
_journal_issue                   13
_journal_name_full               'Chemical Science'
_journal_page_first              4747
_journal_page_last               4752
_journal_paper_doi               10.1039/D0SC07089K
_journal_volume                  12
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H30 O5, C H2 Cl2'
_chemical_formula_sum            'C26 H32 Cl2 O5'
_chemical_formula_weight         495.41
_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     dual
_audit_creation_date             2020-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-17 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.44070(10)
_cell_length_b                   11.69890(10)
_cell_length_c                   28.3425(2)
_cell_measurement_reflns_used    33762
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      74.0820
_cell_measurement_theta_min      3.1160
_cell_volume                     2467.16(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      5.00  31.00   1.00    1.00    --    0.00  38.00 -90.00   26
  2  \w    -35.00  30.00   1.00    1.00    --    0.00 -77.00  60.00   65
  3  \w    -32.00  29.00   1.00    1.00    --    0.00 -77.00-180.00   61
  4  \w     19.00  54.00   1.00    1.00    --    0.00  57.00 -90.00   35
  5  \w    -32.00   0.00   1.00    1.00    --    0.00 -57.00  90.00   32
  6  \w    -22.00   3.00   1.00    1.00    --    0.00  57.00  90.00   25
  7  \w    -83.00 -45.00   1.00    1.00    --    0.00 -77.00  60.00   38
  8  \w    -84.00 -58.00   1.00    1.00    --    0.00 -57.00  90.00   26
  9  \w     53.00  86.00   1.00    1.00    --    0.00  38.00 -90.00   33
 10  \w     41.00  86.00   1.00    1.00    --    0.00  57.00  90.00   45
 11  \w    -19.00  89.00   1.00    1.00    --    0.00  38.00-150.00  108
 12  \w    -89.00  21.00   1.00    1.00    --    0.00 -57.00 -30.00  110
 13  \w     64.00  90.00   1.00    1.00    --   95.80  79.00  12.99   26
 14  \w    139.00 170.00   1.00    1.00    --   95.80  62.00 163.89   31
 15  \w     96.00 184.00   1.00    1.00    --   95.80  80.00  46.04   88
 16  \w     70.00 103.00   1.00    1.00    --   95.80  62.00 163.89   33
 17  \w    130.00 184.00   1.00    1.00    --   95.80  72.00 -10.37   54
 18  \w     64.00  91.00   1.00    1.00    --   95.80  80.00  46.04   27
 19  \w    133.00 181.00   1.00    1.00    --   95.80  60.00-161.68   48
 20  \w     64.00  90.00   1.00    1.00    --   95.80  82.00-120.00   26
 21  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 22  \w     67.00  97.00   1.00    1.00    --   95.80  72.00 -10.37   30
 23  \w     94.00 185.00   1.00    1.00    --   95.80  82.00-120.00   91
 24  \w      6.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00  122
 25  \w     23.00 126.00   1.00    1.00    --   95.80 -82.00  90.00  103
 26  \w     75.00 184.00   1.00    1.00    --   95.80  45.00 -30.00  109
 27  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 150.00   25
 28  \w    106.00 185.00   1.00    1.00    --   95.80  82.00 150.00   79
 29  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 30  \w     75.00 110.00   1.00    1.00    --   95.80  45.00 -60.00   35
 31  \w     44.00 127.00   1.00    1.00    --   95.80 -82.00 150.00   83
 32  \w    146.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   39
 33  \w    120.00 165.00   1.00    1.00    --   95.80  81.00 111.17   45
 34  \w    154.00 185.00   1.00    1.00    --   95.80  59.00-131.73   31
 35  \w     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 36  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 37  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 38  \w     73.00  98.00   1.00    1.00    --   95.80  61.00 150.00   25
 39  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  60.00   26
 40  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 41  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 42  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 43  \w     94.00 120.00   1.00    1.00    --   95.80 -82.00-120.00   26
 44  \w     91.00 116.00   1.00    1.00    --   95.80 -82.00   0.00   25
 45  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  30.00   25
 46  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 47  \w     75.00 111.00   1.00    1.00    --   95.80  45.00 120.00   36
 48  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 -60.00   26
 49  \w    112.00 184.00   1.00    1.00    --   95.80  82.00  97.21   72
 50  \w     63.00  90.00   1.00    1.00    --   95.80  81.00 111.17   27
 51  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 52  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 53  \w     71.00 171.00   1.00    1.00    --   95.80  61.00  30.00  100
 54  \w     65.00 114.00   1.00    1.00    --   95.80  77.00  30.00   49
 55  \w     65.00 104.00   1.00    1.00    --   95.80  77.00  60.00   39
 56  \w     75.00 132.00   1.00    1.00    --   95.80  45.00   0.00   57
 57  \w     75.00 174.00   1.00    1.00    --   95.80  45.00 150.00   99
 58  \w     74.00 119.00   1.00    1.00    --   95.80  61.00-180.00   45
 59  \w    126.00 184.00   1.00    1.00    --   95.80  82.00-180.00   58
 60  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 61  \w     63.00  95.00   1.00    1.00    --   95.80  82.00  97.21   32
 62  \w    114.00 176.00   1.00    1.00    --   95.80  45.00 -60.00   62
 63  \w    136.00 183.00   1.00    1.00    --   95.80  79.00  12.99   47
 64  \w     64.00  89.00   1.00    1.00    --   95.80  79.00-134.30   25
 65  \w     71.00  96.00   1.00    1.00    --   95.80  59.00-131.73   25
 66  \w     71.00 121.00   1.00    1.00    --   95.80  60.00-161.68   50
 67  \w     76.00 153.00   1.00    1.00    --   95.80  34.00-113.70   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0829855000
_diffrn_orient_matrix_UB_12      0.0945146000
_diffrn_orient_matrix_UB_13      -0.0309098000
_diffrn_orient_matrix_UB_21      0.0057114000
_diffrn_orient_matrix_UB_22      0.0804517000
_diffrn_orient_matrix_UB_23      0.0429813000
_diffrn_orient_matrix_UB_31      0.1897400000
_diffrn_orient_matrix_UB_32      -0.0438718000
_diffrn_orient_matrix_UB_33      0.0122404000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            55982
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.023
_diffrn_reflns_theta_max         67.023
_diffrn_reflns_theta_min         3.118
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1789 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+0.6034P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0748
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4337
_reflns_number_total             4385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc07089k2.cif
_cod_data_source_block           exp_1613
_cod_depositor_comments
'Adding full bibliography for 1560502--1560504.cif.'
_cod_database_code               1560504
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.546
_shelx_estimated_absorpt_t_min   0.484
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B), C20(H20A,
 H20B), C21(H21A,H21B), C22(H22A,H22B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C18(H18)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              52222
_shelx_hkl_checksum              24633
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 26.983
_oxdiff_exptl_absorpt_empirical_full_min 0.476