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_4113265
_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         'C17 H15 N O8 S '
_chemical_formula_sum            'C17 H15 N O8 S'
_chemical_formula_weight         393.370
_chemical_name_systematic
;
  Methyl 
(2E)-3-(3-Methoxy-4-{[(2-nitrophenyl)sulfonyl]oxy}phenyl)-2-propenoate

;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                90.097(7)
_cell_angle_beta                 83.386(6)
_cell_angle_gamma                64.270(6)
_cell_formula_units_Z            2
_cell_length_a                   7.5700(10)
_cell_length_b                   7.9500(7)
_cell_length_c                   16.652(2)
_cell_measurement_temperature    296
_cell_volume                     895.27(18)
_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)'
_diffrn_measured_fraction_theta_full 0.836
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_device       'DIP Image plate'
_diffrn_measurement_method       IP
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.09824
_diffrn_orient_matrix_UB_12      0.00003
_diffrn_orient_matrix_UB_13      -0.10978
_diffrn_orient_matrix_UB_21      0.03946
_diffrn_orient_matrix_UB_22      0.12553
_diffrn_orient_matrix_UB_23      0.04643
_diffrn_orient_matrix_UB_31      0.04994
_diffrn_orient_matrix_UB_32      0.00085
_diffrn_orient_matrix_UB_33      -0.03405
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3335
_diffrn_reflns_theta_full        27.18
_diffrn_reflns_theta_max         27.18
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       Prism
_exptl_crystal_F_000             408.0
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.062(6)
_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   1.031
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+0.2665P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                2805
_reflns_number_total             3334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0401702_3.cif
_cod_data_source_block           34f
_cod_original_cell_volume        895.17(18)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C17 H15 N O8 S '
_cod_database_code               4113265