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_4113264
_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 H16 O6 S '
_chemical_formula_sum            'C17 H16 O6 S'
_chemical_formula_weight         348.373
_chemical_name_systematic
;
 Methyl (2E)-3-{3-Methoxy-4-[(phenylsulfonyl)oxy]phenyl}-2-propenoate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3260(2)
_cell_length_b                   8.5000(7)
_cell_length_c                   25.929(2)
_cell_measurement_reflns_used    3280
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      0.00
_cell_volume                     1614.62(19)
_computing_cell_refinement       Scalepack(HKL)
_computing_data_collection       'Mac Science DIP2000'
_computing_data_reduction        'maXus (Mackay et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.922
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device       'Mac Science DIP2000'
_diffrn_measurement_method       IP
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.00430
_diffrn_orient_matrix_UB_12      0.13597
_diffrn_orient_matrix_UB_13      0.00951
_diffrn_orient_matrix_UB_21      -0.02776
_diffrn_orient_matrix_UB_22      0.00708
_diffrn_orient_matrix_UB_23      -0.11377
_diffrn_orient_matrix_UB_31      -0.03741
_diffrn_orient_matrix_UB_32      -0.00181
_diffrn_orient_matrix_UB_33      0.00902
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            3280
_diffrn_reflns_theta_full        27.15
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         0.00
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       'Prism  '
_exptl_crystal_F_000             728.0
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_coef       0.0529(19)
_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   0.716
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.716
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0736
_reflns_number_gt                2258
_reflns_number_total             3271
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0401702_2.cif
_cod_data_source_block           34e
_cod_original_cell_volume        1614.6(2)
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C17 H16 O6 S '
_cod_database_code               4113264