General Approach to Epipolythiodiketopiperazine Alkaloids: Total Synthesis of (+)-Chaetocins A and C and (+)-12,12'-Dideoxychetracin A
Justin Kim; Mohammad Movassaghi; Journal of the American Chemical Society 132 (2010) 14376–14378; doi:10.1021/ja106869s

data_4103319
_publ_section_title
;
 General Approach to Epipolythiodiketopiperazine Alkaloids: Total
 Synthesis of (+)-Chaetocins A and C and (+)-12,12'-Dideoxychetracin A
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14376
_journal_page_last               14378
_journal_paper_doi               10.1021/ja106869s
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C33 H34 N6 O7 S7.77'
_chemical_formula_weight         875.82
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.78280(10)
_cell_length_b                   19.4165(4)
_cell_length_c                   24.7658(5)
_cell_measurement_reflns_used    9175
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.10
_cell_measurement_theta_min      2.89
_cell_volume                     3742.48(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      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            46884
_diffrn_reflns_theta_full        69.89
_diffrn_reflns_theta_max         69.89
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    4.786
_exptl_absorpt_correction_T_max  0.6461
_exptl_absorpt_correction_T_min  0.3278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1817
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         7024
_refine_ls_number_restraints     506
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0569
_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^)+(0.0918P)^2^+5.3303P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1568
_reflns_number_gt                6553
_reflns_number_total             7024
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106869s_si_002.cif
_cod_data_source_block           d8_10096
_cod_database_code               4103319