Asymmetric Total Synthesis of Lancifodilactone G Acetate. 1. Diastereoselective Synthesis of CDEFGH Ring System.
Sun, Tian-Wen; Liu, Dong-Dong; Wang, Kuang-Yu; Tong, Bing-Qi; Xie, Jia-Xin; Jiang, Yan-Long; Li, Yong; Zhang, Bo; Liu, Yi-Fan; Wang, Yuan-Xian; Zhang, Jia-Jun; Chen, Jia-Hua; Yang, Zhen; The Journal of organic chemistry 83 (2018) 6893–6906; doi:10.1021/acs.joc.7b02915

data_4035447
_publ_section_title
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 Asymmetric Total Synthesis of Lancifodilactone G Acetate. 1.
 Diastereoselective Synthesis of CDEFGH Ring System.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6893
_journal_page_last               6906
_journal_paper_doi               10.1021/acs.joc.7b02915
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H30 O6'
_chemical_formula_sum            'C22 H30 O6'
_chemical_formula_weight         390.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.76(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.360(3)
_cell_length_b                   11.2021(16)
_cell_length_c                   15.010(3)
_cell_measurement_reflns_used    1494
_cell_measurement_temperature    291.30(10)
_cell_measurement_theta_max      29.4625
_cell_measurement_theta_min      2.9376
_cell_volume                     1916.4(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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      291.30(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_details
;
  1 omega  -75.00    6.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.2229  -57.0000 -180.0000 81

  2 omega -102.00  -57.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.2229 -178.0000 -120.0000 45
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0046800000
_diffrn_orient_matrix_UB_12      -0.0317847000
_diffrn_orient_matrix_UB_13      0.0422098000
_diffrn_orient_matrix_UB_21      0.0578367000
_diffrn_orient_matrix_UB_22      0.0223647000
_diffrn_orient_matrix_UB_23      0.0241592000
_diffrn_orient_matrix_UB_31      -0.0225334000
_diffrn_orient_matrix_UB_32      0.0500240000
_diffrn_orient_matrix_UB_33      0.0160538000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0927
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5078
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.943
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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    1.353
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0349P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1901
_reflns_number_total             3170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02915_si_002.cif
_cod_data_source_block           exp_173
_cod_original_cell_volume        1916.5(7)
_cod_database_code               4035447
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H24 O6'
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.990
_reflns_odcompleteness_completeness 91.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C21(H21), C11(H11), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C17(H17A,H17B), C23(H23A,H23B), C24(H24A,H24B),
 C18(H18A,H18B), C26(H26A,H26B), C27(H27A,H27B), C25(H25A,H25B)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O28(H28)
;
_olex2_submission_special_instructions 'No special instructions were received'