Total Synthesis of (+)-Lyconadin A and Related Compounds via Oxidative C-N Bond Formation
Scott P. West; Alakesh Bisai; Andrew D. Lim; Raja R. Narayan; Richmond Sarpong; Journal of the American Chemical Society 131 (2009) 11187–11194; doi:10.1021/ja903868n

data_4104836
_publ_section_title
;
 Total Synthesis of (+)-Lyconadin A and Related Compounds via Oxidative
 C-N Bond Formation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11187
_journal_page_last               11194
_journal_paper_doi               10.1021/ja903868n
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C22 H32 N2 O3 '
_chemical_formula_sum            'C22 H32 N2 O3'
_chemical_formula_weight         372.51
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_date             'Wed May 30 13:49:16 2007'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 107.184(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.129(1)
_cell_length_b                   14.816(2)
_cell_length_c                   13.034(1)
_cell_measurement_reflns_used    2994
_cell_measurement_temperature    176.2
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      2.5
_cell_volume                     2053.2(4)
_computing_cell_refinement       'Bruker-AXS SAINT v6.40'
_computing_data_collection       'Bruker-AXS SMART v5.631'
_computing_data_reduction        'Bruker-AXS SAINT v6.40'
_computing_publication_material  teXsan
_computing_structure_refinement  teXsan
_computing_structure_solution    SIR97
_diffrn_measured_fraction_theta_full 0.9941
_diffrn_measured_fraction_theta_max 0.9941
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11803
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       tabular
_exptl_crystal_F_000             808.00
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.818
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2931
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.0003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00022|Fo|^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0530
_refine_ls_wR_factor_ref         0.0494
_reflns_number_gt                2931
_reflns_number_total             4185
_reflns_threshold_expression     F^2^>3.0\s(F^2^)
_cod_data_source_file            ja903868n_si_004.cif
_cod_data_source_block           Alakesh_Bisai_ab-boc-1_at_
_cod_original_cell_volume        2053.3(4)
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_original_formula_sum        'C22 H32 N2 O3 '
_cod_database_code               4104836