Studies toward the Total Synthesis of Dumsin. 2. A Second Generation Approach Resulting in Enantioselective Construction of a Functionalized ABC Subunit of the Tetranortriterpenoid Insect Antifeedant
Leo A. Paquette; Yang Hu; Andreas Luxenburger; Raynauld L. Bishop; Journal of Organic Chemistry 72 (2007) 209–222; doi:10.1021/jo062068o

data_4022664
_publ_section_title
;
 Studies toward the Total Synthesis of Dumsin. 2. A Second Generation
 Approach Resulting in Enantioselective Construction of a Functionalized
 ABC Subunit of the Tetranortriterpenoid Insect Antifeedant
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              209
_journal_page_last               222
_journal_paper_doi               10.1021/jo062068o
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration rmad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C38 H54 O4 Si1'
_chemical_formula_sum            'C38 H54 O4 Si'
_chemical_formula_weight         602.9
_chemical_name_common            'Paquette 1500'
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2006-10-02T14:20:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.509(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.194(2)
_cell_length_b                   8.995(2)
_cell_length_c                   17.869(3)
_cell_measurement_reflns_used    3373
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     1797.5(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.38347E-2
_diffrn_orient_matrix_UB_12      0.891349E-1
_diffrn_orient_matrix_UB_13      -0.59939E-2
_diffrn_orient_matrix_UB_21      -0.736356E-1
_diffrn_orient_matrix_UB_22      0.24306E-2
_diffrn_orient_matrix_UB_23      0.832561E-1
_diffrn_orient_matrix_UB_31      0.417527E-1
_diffrn_orient_matrix_UB_32      0.67261E-2
_diffrn_orient_matrix_UB_33      0.367317E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23079
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.11
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.32
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6274
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.059
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0764P)^2^+0.5235P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                5135
_reflns_number_total             6274
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062068osi20061005_025949.cif
_cod_data_source_block           Paquette1500
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022664