Total Synthesis of (-)-Incarvilline, (+)-Incarvine C, and (-)-Incarvillateine
Masaya Ichikawa; Masaki Takahashi; Sakae Aoyagi; Chihiro Kibayashi; Journal of the American Chemical Society 126 (2004) 16553–16558; doi:10.1021/ja0401702

data_4113267
_publ_contact_author_address
;
School of Pharmacy, Tokyo University of Pharmacy and Life Science,
Horinouchi Hachioji, Tokyo, 192-0392, Japan
;
_publ_contact_author_email       ' kibayasi@ps.toyaku.ac.jp '
_publ_contact_author_name        'Chihiro Kubayashi '
_publ_section_title
;
 Total Synthesis of (-)-Incarvilline, (+)-Incarvine C, and
 (-)-Incarvillateine
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16553
_journal_page_last               16558
_journal_paper_doi               10.1021/ja0401702
_journal_volume                  126
_journal_year                    2004
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C32 H26 N2 O12 '
_chemical_formula_sum            'C32 H26 N2 O12'
_chemical_formula_weight         630.562
_chemical_name_systematic
;
 Bis(4-nitrophenyl) 
 Bis(4-hydroxy-3-methoxyphenyl)-1,2-cyclobutanedicarboxylate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.632(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.931(3)
_cell_length_b                   6.6480(7)
_cell_length_c                   19.006(4)
_cell_measurement_reflns_used    3135
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      1.09
_cell_volume                     1481.6(5)
_computing_cell_refinement       Scalepack(HKL)
_computing_data_collection       'DIP Image plate'
_computing_data_reduction        'maXus (Mackay et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_measured_fraction_theta_full 0.874
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_device       'DIP Image plate'
_diffrn_measurement_method       IP
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.02086
_diffrn_orient_matrix_UB_12      -0.00159
_diffrn_orient_matrix_UB_13      -0.08276
_diffrn_orient_matrix_UB_21      0.01626
_diffrn_orient_matrix_UB_22      -0.14931
_diffrn_orient_matrix_UB_23      0.00697
_diffrn_orient_matrix_UB_31      -0.04833
_diffrn_orient_matrix_UB_32      -0.00629
_diffrn_orient_matrix_UB_33      -0.02199
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3135
_diffrn_reflns_theta_full        27.15
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         1.09
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       Prism
_exptl_crystal_F_000             656.0
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(17)
_refine_ls_extinction_coef       0.033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         3135
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0651P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1305
_reflns_number_gt                1733
_reflns_number_total             3135
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0401702_5.cif
_cod_data_source_block           35
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 21 '
_cod_original_formula_sum        'C32 H26 N2 O12 '
_cod_database_code               4113267