Base-catalyzed Diels-Alder reactions of 2H-pyran-2,5-diones: a mild approach to basiliolide B.
Zhou, Xiongfei; Wu, Wanqing; Liu, Xiaozu; Lee, Chi-Sing; Organic letters 10 (2008) 5525–5528; doi:10.1021/ol8022787

data_1504971
_publ_section_title
;
 Base-catalyzed Diels-Alder reactions of 2H-pyran-2,5-diones: a mild
 approach to basiliolide B.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5525
_journal_page_last               5528
_journal_paper_doi               10.1021/ol8022787
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C16 H24 O8'
_chemical_formula_sum            'C16 H24 O8'
_chemical_formula_weight         344.35
_space_group_IT_number           2
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_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.881(4)
_cell_angle_beta                 91.237(4)
_cell_angle_gamma                95.110(4)
_cell_formula_units_Z            2
_cell_length_a                   6.0385(3)
_cell_length_b                   11.2413(6)
_cell_length_c                   13.3832(8)
_cell_measurement_reflns_used    3060
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8996
_cell_measurement_theta_min      3.3802
_cell_volume                     902.43(9)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics    'WinGX v1.70.01'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Sapphire CCD detector'
_diffrn_measurement_method       '\f and \w 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  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6612
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.39
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED, Oxford Diffraction Ltd.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                2012
_reflns_number_total             3060
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8022787_si_003.cif
_cod_data_source_block           t1
_cod_original_cell_volume        902.42(9)
_cod_original_sg_symbol_H-M      'p -1'
_cod_database_code               1504971