Enantioselective Photocycloaddition of 3-Hydroxyflavones: Total Syntheses and Absolute Configuration Assignments of (+)-Ponapensin and (+)-Elliptifoline
Neil J. Lajkiewicz; Stéphane P. Roche; Baudouin Gerard; John A. Porco; Journal of the American Chemical Society 134 (2012) 13108–13113; doi:10.1021/ja305342f

data_4118476
_publ_section_title
;
 Enantioselective Photocycloaddition of 3-Hydroxyflavones: Total Syntheses
 and Absolute Configuration Assignments of (+)-Ponapensin and
 (+)-Elliptifoline
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13108
_journal_page_last               13113
_journal_paper_doi               10.1021/ja305342f
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C32 H35 N O8, 2(C6 H6)'
_chemical_formula_sum            'C44 H47 N O8'
_chemical_formula_weight         717.83
_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                71.620(4)
_cell_angle_beta                 69.603(4)
_cell_angle_gamma                63.746(4)
_cell_formula_units_Z            2
_cell_length_a                   11.6354(9)
_cell_length_b                   12.6447(10)
_cell_length_c                   15.6781(11)
_cell_measurement_reflns_used    8559
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.52
_cell_volume                     1903.0(3)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega 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  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31176
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     574
_refine_ls_number_reflns         7763
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.6521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                5811
_reflns_number_total             7763
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja305342f_si_001.cif
_cod_data_source_block           porco141
_cod_original_cell_volume        1903.0(2)
_cod_database_code               4118476