Divergent Approach to the Bisanthraquinone Natural Products: Total Synthesis of (S)-Bisoranjidiol and Derivatives from Binaphtho-para-quinones
Erin E. Podlesny; Marisa C. Kozlowski; Journal of Organic Chemistry 78 (2013) 466–476; doi:10.1021/jo302364h

data_4027858
_publ_section_title
;
 Divergent Approach to the Bisanthraquinone Natural Products: Total
 Synthesis of (S)-Bisoranjidiol and Derivatives from
 Binaphtho-para-quinones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              466
_journal_page_last               476
_journal_paper_doi               10.1021/jo302364h
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C17 H12 O6'
_chemical_formula_weight         312.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.977(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7281(9)
_cell_length_b                   26.834(4)
_cell_length_c                   8.6983(14)
_cell_measurement_temperature    143(1)
_cell_volume                     1324.1(4)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14179
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  Shape and scale corrections using equivalent reflections.
   Shape function based on spherical harmonics.
   Highest even and odd order for spherical harmonics:  4  and  3
   Laue group:  2/m
   Friedel opposites are equivalent.
;
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0831P)^2^+0.3930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1363
_reflns_number_gt                2022
_reflns_number_total             2327
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302364h_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/c     '
_cod_database_code               4027858