General Strategy for Stereoselective Synthesis of 1-Substituted Exo,Endo-2,6-Diaryl-3,7-dioxabicyclo[3.3.0]octanes: Total Synthesis of (±)-Gmelinol
Manat Pohmakotr; Attapol Pinsa; Tipwan Mophuang; Patoomratana Tuchinda; Samran Prabpai; Palangpon Kongsaeree; Vichai Reutrakul; Journal of Organic Chemistry 71 (2006) 386–389; doi:10.1021/jo0519110

data_4021370
_publ_section_title
;
 General Strategy for Stereoselective Synthesis of
 1-Substituted Exo,Endo-2,6-Diaryl-3,7-dioxabicyclo[3.3.0]octanes:
 Total Synthesis of (+-)-Gmelinol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              386
_journal_page_last               389
_journal_paper_doi               10.1021/jo0519110
_journal_volume                  71
_journal_year                    2006
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C19 H16 O4'
_chemical_formula_sum            'C19 H16 O4'
_chemical_formula_weight         308.333
_chemical_name_systematic
(3R,3aS,6R,6aS)-3a-methyl-3,6-diphenyl-tetrahydrofuro[3,4-c]furan-1,4-dione
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 101.100(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.9180(7)
_cell_length_b                   11.7246(4)
_cell_length_c                   10.9364(3)
_cell_measurement_reflns_used    4773
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.713
_cell_measurement_theta_min      0.998
_cell_volume                     3135.3(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.05346
_diffrn_orient_matrix_UB_12      -0.07610
_diffrn_orient_matrix_UB_13      0.00575
_diffrn_orient_matrix_UB_21      0.03967
_diffrn_orient_matrix_UB_22      0.02242
_diffrn_orient_matrix_UB_23      -0.07210
_diffrn_orient_matrix_UB_31      0.03157
_diffrn_orient_matrix_UB_32      0.01418
_diffrn_orient_matrix_UB_33      0.02179
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8478
_diffrn_reflns_theta_full        24.74
_diffrn_reflns_theta_max         24.74
_diffrn_reflns_theta_min         1.67
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_recrystallization_method 'slow evaporation'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.7962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                4251
_reflns_number_total             5208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0519110si20050930_053231.cif
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4021370