A General, Convergent Strategy for the Construction of Indolizidine Alkaloids: Total Syntheses of (-)-Indolizidine 223AB and Alkaloid (-)-205B
Amos B. Smith, III; Dae-Shik Kim; Journal of Organic Chemistry 71 (2006) 2547–2557; doi:10.1021/jo052314g

data_4021588
_publ_section_title
;
 A General, Convergent Strategy for the Construction of Indolizidine
 Alkaloids: Total Syntheses of (-)-Indolizidine 223AB and Alkaloid (-)-205B
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2547
_journal_page_last               2557
_journal_paper_doi               10.1021/jo052314g
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C16 H26 I N S2'
_chemical_formula_weight         423.40
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_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                   9.2219(5)
_cell_length_b                   10.6484(5)
_cell_length_c                   17.6602(9)
_cell_measurement_temperature    143(1)
_cell_volume                     1734.20(15)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9013
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    2.079
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5784
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0197
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0193P)^2^+0.1574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0466
_refine_ls_wR_factor_ref         0.0469
_reflns_number_gt                3092
_reflns_number_total             3137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052314gsi20051110_115104.cif
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4021588