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_4113266
_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         'C18 H18 O6 S '
_chemical_formula_sum            'C18 H18 O6 S'
_chemical_formula_weight         362.400
_chemical_name_systematic
;
 Methyl 
(2E)-3-(3-Methoxy-4-{[(4-methylphenyl)sulfonyl]oxy}phenyl)-2-propenoate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 91.735(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.603(2)
_cell_length_b                   8.8580(9)
_cell_length_c                   15.656(2)
_cell_measurement_reflns_used    3639
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.08
_cell_volume                     3410.4(6)
_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 0.902
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device       'DIP Image plate'
_diffrn_measurement_method       IP
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.00754
_diffrn_orient_matrix_UB_12      -0.03374
_diffrn_orient_matrix_UB_13      0.02142
_diffrn_orient_matrix_UB_21      0.00662
_diffrn_orient_matrix_UB_22      0.06133
_diffrn_orient_matrix_UB_23      0.09426
_diffrn_orient_matrix_UB_31      -0.06228
_diffrn_orient_matrix_UB_32      -0.00957
_diffrn_orient_matrix_UB_33      0.01060
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3639
_diffrn_reflns_theta_full        27.13
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1520.0
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.0059(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   1.044
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0700P)^2^+3.4269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                2980
_reflns_number_total             3407
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0401702_4.cif
_cod_data_source_block           34g
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 2/c '
_cod_original_formula_sum        'C18 H18 O6 S '
_cod_database_code               4113266