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_1548240
_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_absolute_configuration ad
_chemical_formula_moiety         'C34 H46 O7'
_chemical_formula_sum            'C34 H46 O7'
_chemical_formula_weight         566.71
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2017-11-21 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   12.4836(2)
_cell_length_b                   12.5791(2)
_cell_length_c                   20.1204(3)
_cell_measurement_reflns_used    23514
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      62.8160
_cell_measurement_theta_min      3.5280
_cell_volume                     3159.56(9)
_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  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.2434   57.0000   30.0000 89

  2 omega   32.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.2434 -178.0000 -120.0000 78

  3 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.2434   57.0000  -60.0000 89

  4 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.2434   57.0000 -120.0000 89

  5 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.2434   77.0000 -180.0000 100

  6 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.2434   57.0000  120.0000 89

  7 omega   19.00  129.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000 -134.8622 110

  8 omega   19.00  129.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000  133.6550 110

  9 omega   19.00  129.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000   45.5231 110

 10 omega   37.00  164.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000 -150.0000 127

 11 omega   22.00  112.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000   60.0000 90

 12 omega   18.00   69.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   30.0000 51

 13 omega   22.00  112.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000  150.0000 90

 14 omega   19.00  127.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -88.0000   80.3267 108

 15 omega   19.00  129.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000 -153.6529 110

 16 omega   79.00  163.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000 -180.0000 84

 17 omega   19.00   77.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -60.0000 58

 18 omega   19.00   77.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -180.0000 58

 19 omega   22.00  112.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000  120.0000 90

 20 omega   19.00   77.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  150.0000 58

 21 omega   61.00  163.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000  -90.0000 102

 22 omega   18.00  163.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000    0.0000   60.0000 145

 23 omega   60.00  161.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -150.0000 101

 24 omega   60.00  161.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  150.0000 101

 25 omega   69.00  159.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -180.0000 90

 26 omega   69.00  159.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -150.0000 90

 27 omega   19.00  129.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000  141.5751 110

 28 omega   61.00  163.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000 -180.0000 102

 29 omega   18.00   90.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  120.0000 72

 30 omega   79.00  163.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  -90.0000 84

 31 omega   19.00   71.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -150.0000 52

 32 omega   39.00   66.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000  150.0000 27

 33 omega  124.00  150.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000  150.0000 26

 34 omega   58.00  114.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000   27.0000   -6.0000 56

 35 omega   21.00   68.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  120.0000 47

 36 omega   66.00   92.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000    6.4979 26

 37 omega   20.00   45.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -95.0000  -90.0000 25

 38 omega   54.00   80.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -95.0000  -90.0000 26

 39 omega   62.00   89.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -120.0000 27

 40 omega   90.00  118.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  -71.9672 28

 41 omega   33.00   76.00   1.0000    1.3450
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  -71.9672 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      -0.0350818000
_diffrn_orient_matrix_UB_12      0.1173896000
_diffrn_orient_matrix_UB_13      -0.0011997000
_diffrn_orient_matrix_UB_21      -0.1109208000
_diffrn_orient_matrix_UB_22      -0.0319700000
_diffrn_orient_matrix_UB_23      0.0270634000
_diffrn_orient_matrix_UB_31      0.0413261000
_diffrn_orient_matrix_UB_32      0.0140658000
_diffrn_orient_matrix_UB_33      0.0715763000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            50336
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        62.813
_diffrn_reflns_theta_max         62.813
_diffrn_reflns_theta_min         4.145
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74933
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0712P)^2^+1.0445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1222
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4934
_reflns_number_total             5062
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04672c2.cif
_cod_data_source_block           caojiaqing_bii41-53xi
_cod_depositor_comments
'Adding full bibliography for 1548236--1548240.cif.'
_cod_original_cell_volume        3159.58(9)
_cod_database_code               1548240
_shelx_shelxl_version_number     2017/1
_cell_oxdiff_angle_alpha         90.004(2)
_cell_oxdiff_angle_beta          89.988(2)
_cell_oxdiff_angle_gamma         90.035(3)
_cell_oxdiff_length_a            12.4785(4)
_cell_oxdiff_length_b            12.5787(4)
_cell_oxdiff_length_c            20.1295(6)
_cell_oxdiff_measurement_reflns_used 23515
_cell_oxdiff_volume              3159.58(17)
_reflns_odcompleteness_completeness 97.24
_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 C(H,H,H,H,H,H) groups, All O(H) groups
2. Others
 Sof(H13A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(H14D)=Sof(H14E)=Sof(H14F)=
 Sof(C13")=Sof(H13")=1-FVAR(1)
 Sof(H13)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(H14A)=Sof(H14B)=Sof(H14C)=
 Sof(C13')=Sof(H13')=FVAR(1)
3.a Riding coordinates:
 O3(H3)
3.b Ternary CH refined with riding coordinates:
 C6'(H6'), C7B(H7B), C13(H13), C13(H13A), C9(H9), C9'(H9'), C13'(H13'),
 C13"(H13")
3.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.d Me refined with riding coordinates:
 C15'(H15A,H15B,H15C), C15'(H15D,H15E,H15F), C14'(H14A,H14B,H14C), C14'(H14D,
 H14E,H14F)
3.e Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10)
3.f Idealised Me refined as rotating group:
 C7'(H7'A,H7'B,H7'C), C10'(H10A,H10B,H10C), C8'(H8'A,H8'B,H8'C), C12'(H12A,
 H12B,H12C), C2'(H2'A,H2'B,H2'C), C4'(H4'A,H4'B,H4'C), C1'(H1'A,H1'B,H1'C),
 C3'(H3'A,H3'B,H3'C), C11'(H11A,H11B,H11C)
3.g Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'