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_1555417
_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         'C15 H18 O7'
_chemical_formula_sum            'C15 H18 O7'
_chemical_formula_weight         310.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 98.176(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1870(4)
_cell_length_b                   8.7702(4)
_cell_length_c                   11.0150(6)
_cell_measurement_reflns_used    1513
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3800
_cell_measurement_theta_min      3.9320
_cell_volume                     687.23(6)
_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 0.952
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_details
;
  1 omega  -88.00    0.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3204  -57.0000    0.0000 88

  2 omega  -88.00   -6.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3204  -57.0000  -90.0000 82

  3 omega  -65.00  -37.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3204 -178.0000   30.0000 28

  4 omega   59.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6485    0.0000  -60.0000 28

  5 omega  -20.00    5.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6485    0.0000  -60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0761329000
_diffrn_orient_matrix_UB_12      -0.0158060000
_diffrn_orient_matrix_UB_13      0.0466141000
_diffrn_orient_matrix_UB_21      -0.0588085000
_diffrn_orient_matrix_UB_22      0.0142421000
_diffrn_orient_matrix_UB_23      0.0453301000
_diffrn_orient_matrix_UB_31      -0.0261715000
_diffrn_orient_matrix_UB_32      -0.0780479000
_diffrn_orient_matrix_UB_33      -0.0011223000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2825
_diffrn_reflns_point_group_measured_fraction_full 0.695
_diffrn_reflns_point_group_measured_fraction_max 0.606
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_min         3.189
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95608
_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    1.499
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 488 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.7(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         1929
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0417P)^2^+0.1160P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0702
_reflns_Friedel_coverage         0.352
_reflns_Friedel_fraction_full    0.399
_reflns_Friedel_fraction_max     0.338
_reflns_number_gt                1866
_reflns_number_total             1929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02845_si_002.cif
_cod_data_source_block           zydtm
_cod_original_cell_volume        687.24(6)
_cod_database_code               1555417
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_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:
 C6(H6), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C21(H21A,H21B), C22(H22A,H22B)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5)
;
_shelx_res_checksum              49684
_shelx_hkl_checksum              16137
_olex2_submission_special_instructions 'No special instructions were received'