Preparation of the 4-hydroxytryptamine scaffold via palladium-catalyzed cyclization: a practical and versatile synthesis of psilocin.
Gathergood, Nicholas; Scammells, Peter J.; Organic letters 5 (2003) 921–923; doi:10.1021/ol0341039

data_1507267
_publ_section_title
;
 Preparation of the 4-hydroxytryptamine scaffold via palladium-catalyzed
 cyclization: a practical and versatile synthesis of psilocin.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              921
_journal_page_last               923
_journal_paper_doi               10.1021/ol0341039
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C33 H42 N2 O3 Si'
_chemical_formula_weight         542.78
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                91.503(1)
_cell_angle_beta                 108.014(1)
_cell_angle_gamma                97.261(1)
_cell_formula_units_Z            2
_cell_length_a                   10.8305(1)
_cell_length_b                   11.1512(2)
_cell_length_c                   13.6330(2)
_cell_measurement_reflns_used    26374
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      3.5
_cell_volume                     1549.51(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.735161E-1
_diffrn_orient_matrix_UB_12      0.668105E-1
_diffrn_orient_matrix_UB_13      0.64626E-2
_diffrn_orient_matrix_UB_21      0.205821E-1
_diffrn_orient_matrix_UB_22      0.49909E-2
_diffrn_orient_matrix_UB_23      0.768571E-1
_diffrn_orient_matrix_UB_31      0.615712E-1
_diffrn_orient_matrix_UB_32      -0.610181E-1
_diffrn_orient_matrix_UB_33      0.54125E-2
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0603
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26374
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         3.54
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         7538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0402P)^2^+0.1803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                5271
_reflns_number_total             7538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0341039si20030120_072956.cif
_cod_data_source_block           k38_02
_cod_database_code               1507267