Protecting-Group-Free Total Synthesis of (-)-Jiadifenolide: Development of a [4 + 1] Annulation toward Multisubstituted Tetrahydrofurans.
Shen, Yang; Li, Linbin; Pan, Zhisheng; Wang, Yinglu; Li, Jundong; Wang, Kuangyu; Wang, Xiance; Zhang, Youyu; Hu, Tianhui; Zhang, Yandong; Organic letters 17 (2015) 5480–5483; doi:10.1021/acs.orglett.5b02845

data_1555416
_publ_section_title
;
 Protecting-Group-Free Total Synthesis of (-)-Jiadifenolide: Development
 of a [4 + 1] Annulation toward Multisubstituted Tetrahydrofurans.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5480
_journal_page_last               5483
_journal_paper_doi               10.1021/acs.orglett.5b02845
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C18 H28 O4 Si'
_chemical_formula_sum            'C18 H28 O4 Si'
_chemical_formula_weight         336.49
_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     direct
_audit_creation_date             2015-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2691(8)
_cell_length_b                   11.4811(10)
_cell_length_c                   21.668(2)
_cell_measurement_reflns_used    1499
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7440
_cell_measurement_theta_min      3.8120
_cell_volume                     1808.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1903
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_details
;
  1 omega  -18.00   51.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6309   77.0000  150.0000 69

  2 omega  -93.00   11.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6309  -38.0000   30.0000 104

  3 omega    6.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0372   77.0000  -90.0000 83

  4 omega    2.00   27.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0372  -99.0000  -60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0423646000
_diffrn_orient_matrix_UB_12      0.0274467000
_diffrn_orient_matrix_UB_13      -0.0256851000
_diffrn_orient_matrix_UB_21      -0.0765021000
_diffrn_orient_matrix_UB_22      -0.0380422000
_diffrn_orient_matrix_UB_23      0.0026631000
_diffrn_orient_matrix_UB_31      -0.0435916000
_diffrn_orient_matrix_UB_32      0.0401171000
_diffrn_orient_matrix_UB_33      0.0200920000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9145
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.151
_diffrn_reflns_theta_min         2.956
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
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    1.236
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1197 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.03(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.879
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0497
_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^)+(0.1000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1379
_reflns_Friedel_coverage         0.648
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.770
_reflns_number_gt                3446
_reflns_number_total             4098
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02845_si_002.cif
_cod_data_source_block           zydsy
_cod_database_code               1555416
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.63
_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
2.a Ternary CH refined with riding coordinates:
 C5(H5), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              28129
_shelx_hkl_checksum              75588
_olex2_submission_special_instructions 'No special instructions were received'