Total Synthesis of (\±)-Trigonoliimine C via Oxidative Rearrangement of an Unsymmetrical Bis-Tryptamine
Xiangbing Qi; Hongli Bao; Uttam K. Tambar; Journal of the American Chemical Society 133 (2011) 10050–10053; doi:10.1021/ja203960b

data_4106358
_publ_section_title
;
 Total Synthesis of (\+-)-Trigonoliimine C via Oxidative Rearrangement of
 an Unsymmetrical Bis-Tryptamine
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10050
_journal_page_last               10053
_journal_paper_doi               10.1021/ja203960b
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C30 H26 N4 O5, C H2 Cl2'
_chemical_formula_sum            'C31 H28 Cl2 N4 O5'
_chemical_formula_weight         607.47
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.908(5)
_cell_angle_beta                 92.052(5)
_cell_angle_gamma                112.872(5)
_cell_formula_units_Z            2
_cell_length_a                   9.934(2)
_cell_length_b                   10.977(2)
_cell_length_c                   14.781(3)
_cell_measurement_reflns_used    16259
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1441.0(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku SCX-Mini with Mercury CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1610
_diffrn_reflns_av_sigmaI/netI    0.1529
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16246
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Abscor. T. Higashi (2001).  The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       plates
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         5049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1969
_refine_ls_R_factor_gt           0.0794
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1930
_reflns_number_gt                2118
_reflns_number_total             5049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja203960b_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4106358