Total Synthesis of (\±)-Spiniferin-1 via a Polyfluoroalkanosulfonyl Fluoride Induced Homoallylic Carbocation Rearrangement Reaction
Kai Ding; Yun-shan Sun; Wei-Sheng Tian; Journal of Organic Chemistry 76 (2011) 1495–1498; doi:10.1021/jo102351k

data_4026094
_publ_section_title
;
 Total Synthesis of (\+-)-Spiniferin-1 via a Polyfluoroalkanosulfonyl
 Fluoride Induced Homoallylic Carbocation Rearrangement Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1495
_journal_page_last               1498
_journal_paper_doi               10.1021/jo102351k
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H26 O6'
_chemical_formula_weight         386.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.972(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.5615(12)
_cell_length_b                   8.3727(9)
_cell_length_c                   11.8537(12)
_cell_measurement_reflns_used    858
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.967
_cell_measurement_theta_min      4.865
_cell_volume                     991.26(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_sigmaI/netI    0.0923
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5692
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76531
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.764
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2159
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.763
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0106P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0516
_refine_ls_wR_factor_ref         0.0581
_reflns_number_gt                1210
_reflns_number_total             2159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102351k_si_002.cif
_cod_data_source_block           cd26181
_cod_original_cell_volume        991.26(18)
_cod_database_code               4026094