Catalytic asymmetric total syntheses of myrtucommuacetalone, myrtucommuacetalone B, and callistrilones A, C, D and E.
Cheng, Min-Jing; Cao, Jia-Qing; Yang, Xin-Yi; Zhong, Li-Ping; Hu, Li-Jun; Lu, Xi; Hou, Bao-Long; Hu, Ya-Jian; Wang, Ying; You, Xue-Fu; Wang, Lei; Ye, Wen-Cai; Li, Chuang-Chuang; Chemical science 9 (2018) 1488–1495; doi:10.1039/c7sc04672c

data_1548236
_publ_section_title
;
 Catalytic asymmetric total syntheses of myrtucommuacetalone,
 myrtucommuacetalone B, and callistrilones A, C, D and E.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              1488
_journal_page_last               1495
_journal_paper_doi               10.1039/c7sc04672c
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C H Cl3, C38 H52 O9'
_chemical_formula_sum            'C39 H53 Cl3 O9'
_chemical_formula_weight         772.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-21 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                94.892(4)
_cell_angle_beta                 105.455(4)
_cell_angle_gamma                113.791(4)
_cell_formula_units_Z            2
_cell_length_a                   12.7541(5)
_cell_length_b                   13.5008(6)
_cell_length_c                   13.6961(6)
_cell_measurement_reflns_used    7120
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.8500
_cell_measurement_theta_min      3.4430
_cell_volume                     2029.61(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -40.00  106.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       33.1184    0.0000   30.0000 146

  2 omega  108.00  162.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000    0.0000  120.0000 54

  3 omega   87.00  113.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -90.0000    4.8737 26

  4 omega   75.00  108.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  -19.2243 33

  5 omega   64.00  129.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  -78.0495 65

  6 omega   66.00  106.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
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  7 omega   52.00   77.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   60.0000 25

  8 omega   45.00   71.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
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  9 omega   40.00   71.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  150.0000 31

 10 omega   36.00  129.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000   84.1488 93

 11 omega   88.00  114.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  172.7701 26

 12 omega   42.00   69.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  172.7701 27

 13 omega   39.00   65.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   90.0000 26

 14 omega   30.00   55.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   30.0000 25

 15 omega   32.00   57.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -90.0000    4.8737 25

 16 omega   30.00   56.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000   60.0000 26

 17 omega   18.00   71.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  -30.0000 53

 18 omega   53.00   88.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  -60.0000 35

 19 omega   47.00  112.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000  -60.0000 65

 20 omega   54.00   86.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000 -180.0000 32

 21 omega   48.00   86.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000 -120.0000 38

 22 omega   27.00   69.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000    0.0000 42

 23 omega   25.00   69.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  -90.0000 44

 24 omega   19.00   70.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000 -120.0000 51

 25 omega    4.00   74.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       33.1184  -99.0000   30.0000 70

 26 omega   19.00   67.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  150.0000 48

 27 omega   38.00   99.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000   90.0000 61

 28 omega   85.00  146.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000   30.0000 61

 29 omega  120.00  159.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -60.0000 39

 30 omega  137.00  162.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  -90.0000 25

 31 omega  124.00  150.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000 -150.0000 26

 32 omega  121.00  150.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  -60.0000 29

 33 omega   86.00  113.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  -60.0000 27

 34 omega   71.00   96.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -60.0000 25

 35 omega   22.00   52.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   60.0000 30

 36 omega   20.00   45.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   90.0000 25

 37 omega   18.00   44.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000    0.0000  120.0000 26

 38 omega   59.00  103.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000  -30.0000 44

 39 omega  -30.00   19.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       33.1184  -38.0000 -180.0000 49

 40 omega  -97.00  -71.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000    0.0000 26

 41 omega -100.00  -69.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000 -180.0000 31

 42 omega -108.00  -65.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -      -33.1184  178.0000   90.0000 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1235063000
_diffrn_orient_matrix_UB_12      -0.0031463000
_diffrn_orient_matrix_UB_13      0.0374708000
_diffrn_orient_matrix_UB_21      0.0301403000
_diffrn_orient_matrix_UB_22      0.0446164000
_diffrn_orient_matrix_UB_23      -0.0938995000
_diffrn_orient_matrix_UB_31      0.0582556000
_diffrn_orient_matrix_UB_32      0.1197148000
_diffrn_orient_matrix_UB_33      0.0638871000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17119
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        62.749
_diffrn_reflns_theta_max         62.749
_diffrn_reflns_theta_min         3.431
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
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_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.844
_refine_diff_density_min         -0.886
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         6474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0914
_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^)+(0.1804P)^2^+1.8532P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2714
_refine_ls_wR_factor_ref         0.2842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5545
_reflns_number_total             6474
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04672c2.cif
_cod_data_source_block           chenpeng_a1(34-48)
_cod_depositor_comments
'Adding full bibliography for 1548236--1548240.cif.'
_cod_original_cell_volume        2029.59(16)
_cod_database_code               1548236
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 96.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60
_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. Others
 Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=
 Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C20)=
 Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C46(H46), C8'(H8'), C9(H9), C10(H10), C17(H17A), C18(H18), C18A(H18A)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.c Idealised Me refined as rotating group:
 C9'(H9'A,H9'B,H9'C), C10'(H10A,H10B,H10C), C14'(H14A,H14B,H14C), C13'(H13A,
 H13B,H13C), C12'(H12A,H12B,H12C), C11'(H11C,H11D,H11E), C19(H19A,H19B,H19C),
 C19A(H19D,H19E,H19F), C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F), C22(H22A,H22B,
 H22C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,
 H25B,H25C), C26(H26A,H26B,H26C)
3.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'