Total Synthesis of Enantiopure Phalarine via a Stereospecific Pictet-Spengler Reaction: Traceless Transfer of Chirality from l-Tryptophan
John D. Trzupek; Dongjoo Lee; Brendan M. Crowley; Vasilios M. Marathias; Samuel J. Danishefsky; Journal of the American Chemical Society 132 (2010) 8506–8512; doi:10.1021/ja1030968

data_4102573
_publ_section_title
;
 Total Synthesis of Enantiopure Phalarine via a Stereospecific
 Pictet-Spengler Reaction: Traceless Transfer of Chirality from
 l-Tryptophan
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8506
_journal_page_last               8512
_journal_paper_doi               10.1021/ja1030968
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C34 H32 N2 O6 S'
_chemical_formula_weight         596.68
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.159(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.841(3)
_cell_length_b                   11.389(3)
_cell_length_c                   18.565(4)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.32
_cell_volume                     2918.8(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            45567
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_correction_T_min  0.8553
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         8888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0597P)^2^+1.1069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                6019
_reflns_number_total             8888
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1030968_si_002.cif
_cod_data_source_block           14s10
_cod_original_cell_volume        2919.0(11)
_cod_database_code               4102573