Intramolecular Silicon-Assisted Cross-Coupling: Total Synthesis of (+)-Brasilenyne
Scott E. Denmark; Shyh-Ming Yang; Journal of the American Chemical Society 124 (2002) 15196–15197; doi:10.1021/ja028936q

data_4115408
_publ_section_title
;
 Intramolecular Silicon-Assisted Cross-Coupling: Total Synthesis of
 (+)-Brasilenyne
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15196
_journal_page_last               15197
_journal_paper_doi               10.1021/ja028936q
_journal_volume                  124
_journal_year                    2002
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H20 O9 Si Co2'
_chemical_formula_sum            'C18 H20 Co2 O9 Si'
_chemical_formula_weight         526.29
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_audit_update_record
; 
? 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.747(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3625(10)
_cell_length_b                   32.698(4)
_cell_length_c                   8.8068(11)
_cell_measurement_reflns_used    1006
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      24.54
_cell_measurement_theta_min      2.49
_cell_volume                     2293.5(5)
_computing_cell_refinement       'SAINT V6 (Bruker, 2001)'
_computing_data_collection       'SMART V5 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6 (Bruker, 2000)'
_computing_publication_material  'CIFTAB (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL V6 (Bruker, 2000)'
_computing_structure_solution    'SHELXTL V6 (Bruker, 2000)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  p72ra
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0867
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12463
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.43
_diffrn_standards_decay_%        3.4
_diffrn_standards_interval_time  395
_diffrn_standards_number         263
_exptl_absorpt_coefficient_mu    1.542
_exptl_absorpt_correction_T_max  0.8798
_exptl_absorpt_correction_T_min  0.7524
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Bruker, 2000)'
_exptl_crystal_colour            ruby
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       prism_cut
_exptl_crystal_F_000             1072
_exptl_crystal_id                p72ra
_exptl_crystal_preparation
; 
The data crystal was mounted using ??oil (Parantone-N, Exxon) to a 
thin glass fiber with the (??) scattering planes roughly normal 
to the spindle axis. 
;
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.045(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         8112
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.932
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0665
_reflns_number_gt                5924
_reflns_number_total             8112
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja028936q-2_s2.cif
_cod_data_source_block           p72ra
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               4115408