Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and Welwitindolinones via a Redox Economic Approach
Jeremy M. Richter; Yoshihiro Ishihara; Takeshi Masuda; Brandon W. Whitefield; Tomás Llamas; Antti Pohjakallio; Phil S. Baran; Journal of the American Chemical Society 130 (2008) 17938–17954; doi:10.1021/ja806981k

data_4108946
_publ_section_title
;
 Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and
 Welwitindolinones via a Redox Economic Approach
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17938
_journal_page_last               17954
_journal_paper_doi               10.1021/ja806981k
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C23 H25 Cl N O'
_chemical_formula_weight         366.89
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 120.61(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.552(4)
_cell_length_b                   8.9917(18)
_cell_length_c                   15.525(3)
_cell_measurement_reflns_used    2212
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.92
_cell_measurement_theta_min      2.64
_cell_volume                     2108.8(10)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7841
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.52
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_meas      0
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_method     riding
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3700
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.108
_refine_ls_shift/su_mean         0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.1500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1303
_reflns_number_gt                2405
_reflns_number_total             3700
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja806981k_si_008.cif
_cod_data_source_block           jeri
_cod_original_cell_volume        2108.7(7)
_cod_database_code               4108946