Formal Homoiodo Allylsilane Annulations: Dual Total Syntheses of (\±)-Hirsutene and (\±)-Capnellene
Shou-Jie Shen; Wei-Dong Z. Li; Journal of Organic Chemistry 78 (2013) 7112–7120; doi:10.1021/jo4009854

data_4028437
_publ_section_title
;
 Formal Homoiodo Allylsilane Annulations: Dual Total Syntheses of
 (\+-)-Hirsutene and (\+-)-Capnellene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7112
_journal_page_last               7120
_journal_paper_doi               10.1021/jo4009854
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C15 H26 O3'
_chemical_formula_weight         254.36
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 94.11(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.18(5)
_cell_length_b                   9.99(3)
_cell_length_c                   7.58(2)
_cell_measurement_reflns_used    981
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.09
_cell_measurement_theta_min      2.30
_cell_volume                     1449(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3554
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(5)
_refine_ls_extinction_coef       0.006(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1573
_refine_ls_R_factor_gt           0.1117
_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^)+(0.3000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3156
_refine_ls_wR_factor_ref         0.3815
_reflns_number_gt                1569
_reflns_number_total             2633
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4009854_si_001.cif
_cod_data_source_block           c2
_cod_database_code               4028437