Enantioselective Total Synthesis of (+)-Gliocladine C: Convergent Construction of Cyclotryptamine-Fused Polyoxopiperazines and a General Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine Precursors
John E. DeLorbe; Salman Y. Jabri; Steven M. Mennen; Larry E. Overman; Fang-Li Zhang; Journal of the American Chemical Society 133 (2011) 6549–6552; doi:10.1021/ja201789v

data_4106084
_publ_section_title
;
 Enantioselective Total Synthesis of (+)-Gliocladine C: Convergent
 Construction of Cyclotryptamine-Fused Polyoxopiperazines and a General
 Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine
 Precursors
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6549
_journal_page_last               6552
_journal_paper_doi               10.1021/ja201789v
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C26.5 H25 Cl3 N4 O4 S2'
_chemical_formula_weight         633.98
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 105.5710(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.4546(11)
_cell_length_b                   11.2020(7)
_cell_length_c                   29.4320(19)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.43
_cell_measurement_theta_min      2.20
_cell_volume                     5543.5(6)
_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      93(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            62392
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  0.9490
_exptl_absorpt_correction_T_min  0.8315
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2616
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.129
_refine_diff_density_min         -1.475
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     718
_refine_ls_number_reflns         12243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1031P)^2^+7.8240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1729
_reflns_number_gt                9856
_reflns_number_total             12243
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja201789v_si_003.cif
_cod_data_source_block           leo232
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_formula_sum        'C26.50 H25 Cl3 N4 O4 S2'
_cod_database_code               4106084