Syntheses of the Stemona Alkaloids (\±)-Stenine, (\±)-Neostenine, and (\±)-13-Epineostenine Using a Stereodivergent Diels-Alder/Azido-Schmidt Reaction
Kevin J. Frankowski; Jennifer E. Golden; Yibin Zeng; Yao Lei; Jeffrey Aubé; Journal of the American Chemical Society 130 (2008) 6018–6024; doi:10.1021/ja800574m

data_4107747
_publ_contact_author
; 
   Prof. Jeffrey Aub\'e 
   Department of Medicinal Chemistry -- University of Kansas 
   Malott Hall 
   1251 Wescoe Hall Dr, Rm 4070 
   Lawrence, KS  66045-7582  USA 
;
_publ_contact_author_email       jaube@ku.edu
_publ_contact_author_fax         1(785)8645326
_publ_contact_author_phone       1(785)8644496
_publ_section_title
;
 Syntheses of the Stemona Alkaloids (\+-)-Stenine, (\+-)-Neostenine, and
 (\+-)-13-Epineostenine Using a Stereodivergent Diels-Alder/Azido-Schmidt
 Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6018
_journal_page_last               6024
_journal_paper_doi               10.1021/ja800574m
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C17 H27 N O2'
_chemical_formula_weight         277.40
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.420(2)
_cell_angle_beta                 109.421(2)
_cell_angle_gamma                111.490(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2660(8)
_cell_length_b                   9.7945(8)
_cell_length_c                   9.8086(8)
_cell_measurement_reflns_used    4147
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.31
_cell_volume                     743.78(11)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9683
_diffrn_reflns_theta_full        30.57
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0742P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                3719
_reflns_number_total             4522
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja800574m-file005.cif
_cod_data_source_block           k94d
_cod_database_code               4107747