Asymmetric Total Synthesis of Caribenol A via an Intramolecular Diels-Alder Reaction
Jing-Chun Han; Lian-Zhu Liu; Yuan-Yuan Chang; Guo-Zong Yue; Jie Guo; Li-Yan Zhou; Chuang-Chuang Li; Zhen Yang; Journal of Organic Chemistry 78 (2013) 5492–5504; doi:10.1021/jo4006156

data_4028303
_publ_section_title
;
 Asymmetric Total Synthesis of Caribenol A via an Intramolecular
 Diels-Alder Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5492
_journal_page_last               5504
_journal_paper_doi               10.1021/jo4006156
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C20 H28 O4'
_chemical_formula_sum            'C20 H28 O4'
_chemical_formula_weight         332.44
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.2811(2)
_cell_length_b                   9.4985(5)
_cell_length_c                   31.822(2)
_cell_measurement_reflns_used    7359
_cell_measurement_temperature    298
_cell_measurement_theta_max      67.40
_cell_measurement_theta_min      7.20
_cell_volume                     1898.53(17)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku Saturn70 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            3094
_diffrn_reflns_theta_full        67.88
_diffrn_reflns_theta_max         67.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       prism
_exptl_crystal_F_000             720.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.506
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0776
_refine_ls_shift/su_max          0.550
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2436
_reflns_number_gt                1773
_reflns_number_total             3094
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo4006156_si_005.cif
_cod_data_source_block           '__20120410hanjingchun'
_cod_database_code               4028303