Asymmetric Total Synthesis of (-)-Azaspirene, a Novel Angiogenesis Inhibitor
Yujiro Hayashi; Mitsuru Shoji; Junichiro Yamaguchi; Kenji Sato; Shinpei Yamaguchi; Takasuke Mukaiyama; Ken Sakai; Yukihiro Asami; Hideaki Kakeya; Hiroyuki Osada; Journal of the American Chemical Society 124 (2002) 12078–12079; doi:10.1021/ja0276826

data_4115201
_publ_contact_author
;
    Dr Ken Sakai
    Department of Applied Chemistry
    Faculty of Science
    Tokyo University of Science
    Kagurazaka 1-3, Shinjuku-ku
    Tokyo 162-8601, Japan
;
_publ_contact_author_email       ksakai@rs.kagu.tus.ac.jp
_publ_contact_author_fax         '81 3 3260 4670'
_publ_contact_author_phone       '81 3 3260 4670'
_publ_section_title
;
 Asymmetric Total Synthesis of (-)-Azaspirene, a Novel Angiogenesis
 Inhibitor
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12078
_journal_page_last               12079
_journal_paper_doi               10.1021/ja0276826
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety         'C24 H27 N O4'
_chemical_formula_sum            'C24 H27 N O4'
_chemical_formula_weight         393.47
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2002/08/28
_audit_creation_method           'SHELXL97-2 (Sheldrick, 1997)'
_audit_update_record
;
2002/08/28     text and data added by Ken Sakai
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.643(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.404(3)
_cell_length_b                   7.941(2)
_cell_length_c                   12.843(3)
_cell_measurement_reflns_used    4444
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      1.65
_cell_volume                     1120.0(5)
_computing_cell_refinement       'SMART & SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics
;
SHELXTL (Bruker, 1998), TEXSAN (Molecular Structure Corporation, Rigaku
Corporation, 1998) & KENX (Sakai, 2000)
;
_computing_publication_material  'SHELXL97-2 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0862
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7922
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.65
_diffrn_standards_decay_%
;
103 reflections were remeasured after the data collection which showed no
decay in the period.
;
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.969908
_exptl_absorpt_correction_T_min  0.689384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.8(14)
_refine_ls_extinction_coef       0.000(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5002
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          3.690
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1713
_reflns_number_gt                3567
_reflns_number_total             5002
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0276826_s2_1.cif
_cod_data_source_block           azaspirene
_cod_database_code               4115201