An Oxidative Dearomatization-Induced [5 + 2] Cascade Enabling the Syntheses of α-Cedrene, α-Pipitzol, and sec-Cedrenol
Jason C. Green; Thomas R. R. Pettus; Journal of the American Chemical Society 133 (2011) 1603–1608; doi:10.1021/ja109925g

data_4105607
_publ_section_title
;
 An Oxidative Dearomatization-Induced [5 + 2] Cascade Enabling the
 Syntheses of \a-Cedrene, \a-Pipitzol, and sec-Cedrenol
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1603
_journal_page_last               1608
_journal_paper_doi               10.1021/ja109925g
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C17 H24 O3'
_chemical_formula_weight         276.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 101.059(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8538(11)
_cell_length_b                   10.9367(14)
_cell_length_c                   16.390(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1557.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scan'
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11831
_diffrn_reflns_theta_full        26.55
_diffrn_reflns_theta_max         26.55
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.369
_exptl_absorpt_correction_T_min  0.187
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'psi scan'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.422
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.422
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.097
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1557
_reflns_number_gt                2047
_reflns_number_total             3100
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja109925g_si_003.cif
_cod_data_source_block           petm
_cod_database_code               4105607