Novel Skeleton Transformation Reaction of α-Pyrone Derivatives to Spirobicyclo[3.1.0]hexane Derivatives Using Dimethylsulfoxonium Methylide.
Miura, Takuya; Yadav, Navnath Dnyanoba; Iwasaki, Hiroki; Ozeki, Minoru; Kojima, Naoto; Yamashita, Masayuki; Organic letters 14 (2012) 6048–6051; doi:10.1021/ol302942m

data_1508780
_publ_section_title
;
 Novel Skeleton Transformation Reaction of \a-Pyrone Derivatives to
 Spirobicyclo[3.1.0]hexane Derivatives Using Dimethylsulfoxonium
 Methylide.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6048
_journal_page_last               6051
_journal_paper_doi               10.1021/ol302942m
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C20 H21 Br O4'
_chemical_formula_sum            'C20 H21 Br O4'
_chemical_formula_weight         405.29
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                65.718(4)
_cell_angle_beta                 84.358(3)
_cell_angle_gamma                78.742(4)
_cell_formula_units_Z            2
_cell_length_a                   7.1334(8)
_cell_length_b                   11.0837(14)
_cell_length_c                   12.6786(13)
_cell_measurement_reflns_used    5597
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.19
_cell_volume                     895.98(18)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8892
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.322
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             416.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.720
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4068
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0492P)^2^+1.0720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1617
_reflns_number_gt                2463
_reflns_number_total             4068
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol302942m_si_002.cif
_cod_data_source_block           SR-007
_cod_database_code               1508780