Total Synthesis of Natural Enantiomers of Heliespirones A and Cviathe Diastereoselective Intramolecular Hosomi-Sakurai Reaction
Akari Miyawaki; Daisuke Kikuchi; Masu Niki; Yuki Manabe; Makoto Kanematsu; Hiromasa Yokoe; Masahiro Yoshida; Kozo Shishido; Journal of Organic Chemistry 77 (2012) 8231–8243; doi:10.1021/jo3016055

data_4027530
_publ_section_title
;
 Total Synthesis of Natural Enantiomers of Heliespirones A and Cviathe
 Diastereoselective Intramolecular Hosomi-Sakurai Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8231
_journal_page_last               8243
_journal_paper_doi               10.1021/jo3016055
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C15 H20 O4 '
_chemical_formula_sum            'C15 H20 O4'
_chemical_formula_weight         264.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90
_cell_angle_beta                 105.66(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.527(3)
_cell_length_b                   22.527(9)
_cell_length_c                   9.912(4)
_cell_measurement_reflns_used    10982
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.2
_cell_volume                     1403.3(10)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9970
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.077
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9901
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       platelet
_exptl_crystal_F_000             568.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.39
_refine_ls_extinction_coef       32(25)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2546
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0001Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                1366
_reflns_number_total             2552
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo3016055_si_002_2.cif
_cod_data_source_block           '_AMA-6-183-2-2____________'
_cod_original_cell_volume        1403(1)
_cod_original_formula_sum        'C15 H20 O4 '
_cod_database_code               4027530