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_4113263
_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_formula_moiety         'C36 H36 O12 S2'
_chemical_formula_sum            'C36 H36 O12 S2'
_chemical_formula_weight         724.77
_chemical_name_systematic
; 
 Dimethyl 
 2,4-Bis(3-methoxy-4-{[(4-methylphenyl)sulfonyl]oxy}phenyl)-1,3-cyclobutanedi 
 carboxylate
 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 91.455(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.8720(6)
_cell_length_b                   16.940(3)
_cell_length_c                   8.902(2)
_cell_measurement_reflns_used    4185
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      1.90
_cell_volume                     2091.2(6)
_computing_cell_refinement
;        
DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) 
;
_computing_data_collection
;
DIP2000 software Xpress (MAC Science, 1989)
;
_computing_data_reduction
;
DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) 
;
_computing_molecular_graphics    'maXus (Mackay et al., 1999)'
_computing_publication_material  'maXus (Mackay et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et al, 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.898
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Mac Science DIP2000'
_diffrn_measurement_method       ' phi scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4185
_diffrn_reflns_theta_full        27.18
_diffrn_reflns_theta_max         27.18
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0683
_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^)+(0.1532P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1908
_refine_ls_wR_factor_ref         0.2071
_reflns_number_gt                2741
_reflns_number_total             4185
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0401702_1.cif
_cod_data_source_block           38
_cod_database_code               4113263