Asymmetric Total Synthesis of Lancifodilactone G Acetate. 2. Final Phase and Completion of the Total Synthesis.
Wang, Kuang-Yu; Liu, Dong-Dong; Sun, Tian-Wen; Lu, Yong; Zhang, Su-Lei; Li, Yuan-He; Han, Yi-Xin; Liu, Hao-Yuan; Peng, Cheng; Wang, Qin-Yang; Chen, Jia-Hua; Yang, Zhen; The Journal of organic chemistry 83 (2018) 6907–6923; doi:10.1021/acs.joc.7b02917

data_4035444
_publ_section_title
;
 Asymmetric Total Synthesis of Lancifodilactone G Acetate. 2. Final Phase
 and Completion of the Total Synthesis.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6907
_journal_page_last               6923
_journal_paper_doi               10.1021/acs.joc.7b02917
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C30 H54 O6 Si2'
_chemical_formula_sum            'C30 H54 O6 Si2'
_chemical_formula_weight         566.91
_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     iterative
_audit_creation_date             2017-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.47108(12)
_cell_length_b                   11.24253(17)
_cell_length_c                   30.7140(4)
_cell_measurement_reflns_used    41489
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3690
_cell_measurement_theta_min      3.8650
_cell_volume                     3270.39(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -114.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556  -77.0000  150.0000 107

  2 omega -114.00  -70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556 -149.0000  165.0000 44

  3 omega  -77.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556  -77.0000 -120.0000 69

  4 omega  -99.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556  -77.0000  -30.0000 90

  5 omega  -50.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556   38.0000 -150.0000 86

  6 omega  -67.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556  -77.0000   60.0000 57

  7 omega -101.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556  -38.0000   30.0000 80

  8 omega  -50.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556   38.0000  120.0000 86

  9 omega -110.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556  -38.0000 -180.0000 93

 10 omega  -80.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556  -57.0000  -30.0000 67

 11 omega -104.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556 -178.0000  -90.0000 69

 12 omega   62.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3556 -178.0000    0.0000 67

 13 omega   88.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3556  178.0000 -180.0000 37

 14 omega    2.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3556   91.0000 -164.6853 25

 15 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 26

 16 omega   82.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   69.0000  -10.2498 25

 17 omega   82.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   64.0000  -30.7905 26

 18 omega   81.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   71.0000 -146.8628 82

 19 omega   80.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   73.0000 -159.1798 26

 20 omega  131.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   64.0000  -45.9018 47

 21 omega   83.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   57.0000  164.5291 27

 22 omega   79.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 98

 23 omega   85.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 41

 24 omega   79.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 25

 25 omega  113.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 36

 26 omega   30.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -60.0000 72

 27 omega   48.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   90.0000 94

 28 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 26

 29 omega  142.00  168.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 26

 30 omega   83.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 91

 31 omega   82.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   62.0000   43.5282 26

 32 omega   80.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 25

 33 omega   29.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -120.0000 80

 34 omega   83.00  153.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   57.0000   75.5418 70

 35 omega   82.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   64.0000  -45.9018 26

 36 omega   55.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   60.0000 61

 37 omega  110.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 67

 38 omega   79.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 26

 39 omega   83.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -120.0000 59

 40 omega   79.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 26

 41 omega   30.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000    0.0000 64

 42 omega   79.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 26

 43 omega  138.00  165.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 27

 44 omega   79.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 95

 45 omega   81.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   69.0000   22.8129 26

 46 omega   33.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   90.0000 68

 47 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 26

 48 omega  128.00  153.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 25

 49 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 26

 50 omega   79.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 26

 51 omega  109.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 68

 52 omega   86.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 25

 53 omega   86.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 85

 54 omega   85.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 59

 55 omega   83.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 60

 56 omega   79.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 27

 57 omega   79.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 26

 58 omega   83.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 76

 59 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 26

 60 omega   81.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 32

 61 omega   81.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   69.0000   93.6480 26

 62 omega   84.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   60.0000 -112.5942 93

 63 omega   85.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   50.0000 -157.6528 26

 64 omega  -70.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556   57.0000    0.0000 104

 65 omega -114.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556  -57.0000    0.0000 103

 66 omega  -50.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3556   38.0000  -90.0000 86

 67 omega   -6.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3556   19.0000  -60.0000 128

 68 omega    2.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3556   91.0000 -164.6853 27

 69 omega    3.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3556   88.0000  121.7572 30

 70 omega    1.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3556  -99.0000  150.0000 81

 71 omega    1.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3556  -99.0000   30.0000 81
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0301676000
_diffrn_orient_matrix_UB_12      -0.0014643000
_diffrn_orient_matrix_UB_13      0.0492922000
_diffrn_orient_matrix_UB_21      -0.1440167000
_diffrn_orient_matrix_UB_22      -0.0596770000
_diffrn_orient_matrix_UB_23      0.0081610000
_diffrn_orient_matrix_UB_31      0.0692931000
_diffrn_orient_matrix_UB_32      -0.1233258000
_diffrn_orient_matrix_UB_33      -0.0045502000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            69231
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         72.116
_diffrn_reflns_theta_min         4.187
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.284
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.151
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          2.5
_exptl_crystal_size_mid          2.5
_exptl_crystal_size_min          2.5
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 2749 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         6439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0550P)^2^+0.8160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6392
_reflns_number_total             6439
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02917_si_003.cif
_cod_data_source_block           exp_8020
_cod_original_cell_volume        3270.39(7)
_cod_database_code               4035444
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C30 H54 O6 Si2'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C12(H12), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C25(H25a,H25b), C34(H34a,H34b), C43(H43a,H43b), C48(H48a,H48b),
 C53(H53a,H53b), C57(H57a,H57b), C65(H65a,H65b), C66(H66a,H66b), C71(H71a,H71b)
2.c X=CH2 refined with riding coordinates:
 C110(H11a,H11b)
2.d Idealised Me refined as rotating group:
 C51(H51a,H51b,H51c), C85(H85a,H85b,H85c), C86(H86a,H86b,H86c), C91(H91a,H91b,
 H91c), C96(H96a,H96b,H96c), C102(H10a,H10b,H10c), C103(H10d,H10e,H10f),
 C108(H10g,H10h,H10i), C116(H11c,H11d,H11e), C118(H11f,H11g,H11h)
;
_olex2_submission_special_instructions 'No special instructions were received'