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_4028300
_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         'C26 H29 N O7'
_chemical_formula_sum            'C26 H29 N O7'
_chemical_formula_weight         467.52
_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                70.258(5)
_cell_angle_beta                 79.287(6)
_cell_angle_gamma                69.189(5)
_cell_formula_units_Z            2
_cell_length_a                   8.94700(10)
_cell_length_b                   10.28630(10)
_cell_length_c                   14.9572(10)
_cell_measurement_reflns_used    15006
_cell_measurement_temperature    298
_cell_measurement_theta_max      67.80
_cell_measurement_theta_min      6.70
_cell_volume                     1207.70(10)
_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 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0424
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4232
_diffrn_reflns_theta_full        67.81
_diffrn_reflns_theta_max         67.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       prism
_exptl_crystal_F_000             496.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     351
_refine_ls_number_reflns         4221
_refine_ls_number_restraints     20
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0631P)^2^+0.2942P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1395
_reflns_number_gt                3488
_reflns_number_total             4221
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo4006156_si_002.cif
_cod_data_source_block           '__20120628hanjingchun'
_cod_database_code               4028300