Total Synthesis of the Quinone Epoxide Dimer (+)-Torreyanic Acid: Application of a Biomimetic Oxidation/Electrocyclization/Diels-Alder Dimerization Cascade1
Chaomin Li; Richard P. Johnson; John A. Porco; Journal of the American Chemical Society 125 (2003) 5095–5106; doi:10.1021/ja021396c

data_4113682
_publ_contact_author
;
     John A. Porco, Jr.
        Department of Chemistry and Center for Streamlined Synthesis
    590 Commonwealth Avenue
    Boston, MA 02215
        USA
;
_publ_contact_author_email       porco@chem.bu.edu
_publ_section_title
;
 Total Synthesis of the Quinone Epoxide Dimer (+)-Torreyanic Acid:
 Application of a Biomimetic Oxidation/Electrocyclization/Diels-Alder
 Dimerization Cascade1
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5095
_journal_page_last               5106
_journal_paper_doi               10.1021/ja021396c
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C38 H49 O8'
_chemical_formula_weight         633.77
_chemical_name_common            'Torreyanic Acid'
_chemical_name_systematic
; 
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.429(5)
_cell_angle_beta                 78.351(5)
_cell_angle_gamma                73.558(5)
_cell_formula_units_Z            2
_cell_length_a                   8.1252(12)
_cell_length_b                   13.613(2)
_cell_length_c                   16.659(3)
_cell_measurement_temperature    173(2)
_cell_volume                     1725.4(5)
_computing_cell_refinement       SAINT+
_computing_data_collection       SMART
_computing_data_reduction        SAINT+
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker 1K CCD'
_diffrn_measurement_method       '0.45 deg. omega scan'
_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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8486
_diffrn_reflns_theta_full        21.49
_diffrn_reflns_theta_max         21.49
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.810194
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       needle
_exptl_crystal_F_000             682
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          1.410
_refine_ls_shift/su_mean         0.062
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0922P)^2^+1.0134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1586
_reflns_number_gt                2662
_reflns_number_total             3960
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja021396c_3.cif
_cod_data_source_block           porco3
_cod_original_cell_volume        1725.4(4)
_cod_database_code               4113682