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_4118477
_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         'C36 H40 N2 O8, H2 0'
_chemical_formula_sum            'C36 H42 N2 O9'
_chemical_formula_weight         646.72
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-06-24 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.1823(14)
_cell_length_b                   12.2311(7)
_cell_length_c                   24.7388(13)
_cell_measurement_reflns_used    9098
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.760
_cell_measurement_theta_min      3.574
_cell_volume                     7317.1(7)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'OLEX2 (Dolmanov, et al. 2009)'
_computing_publication_material  'PublCIF v.1.9.5_c (IUCr)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            148848
_diffrn_reflns_theta_full        66.51
_diffrn_reflns_theta_max         66.51
_diffrn_reflns_theta_min         3.57
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_description       prism
_exptl_crystal_F_000             2752
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.090
_refine_diff_density_max         1.004
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         6426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0609
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0747P)^2^+12.3954P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                5972
_reflns_number_total             6426
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja305342f_si_002.cif
_cod_data_source_block           neil1a_0ma
_cod_database_code               4118477