Efficient synthesis of fused bicyclic glutarimides. Its application to (+/-)-alloyohimbane and louisianin D.
Chen, Hung-Wei; Hsu, Ru-Ting; Chang, Meng-Yang; Chang, Nein-Chen; Organic letters 8 (2006) 3033–3035; doi:10.1021/ol060958k

data_1506045
_publ_section_title
;
 Efficient synthesis of fused bicyclic glutarimides. Its application to
 (+/-)-alloyohimbane and louisianin D.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3033
_journal_page_last               3035
_journal_paper_doi               10.1021/ol060958k
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C22 H23 N O4 S'
_chemical_formula_weight         397.47
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 97.737(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.552(2)
_cell_length_b                   7.7459(8)
_cell_length_c                   13.2549(14)
_cell_measurement_reflns_used    3939
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.358
_cell_measurement_theta_min      2.636
_cell_volume                     1989.2(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10876
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.346
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0509
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1678
_reflns_number_gt                2739
_reflns_number_total             3912
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060958ksi20060421_062130.cif
_cod_data_source_block           h816-1m
_cod_database_code               1506045