Total Syntheses of Drimane-Type Sesquiterpenoids Enabled by a Gold-Catalyzed Tandem Reaction
Hang Shi; Lichao Fang; Ceheng Tan; Lili Shi; Weibin Zhang; Chuang-chuang Li; Tuoping Luo; Zhen Yang; Journal of the American Chemical Society 133 (2011) 14944–14947; doi:10.1021/ja206837j

data_4106840
_publ_section_title
;
 Total Syntheses of Drimane-Type Sesquiterpenoids Enabled by a
 Gold-Catalyzed Tandem Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14944
_journal_page_last               14947
_journal_paper_doi               10.1021/ja206837j
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C20 H23 N O5'
_chemical_formula_weight         357.39
_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                 110.0900(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.3171(10)
_cell_length_b                   8.9956(7)
_cell_length_c                   12.4459(8)
_cell_measurement_temperature    298(2)
_cell_volume                     1820.8(2)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega 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  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7470
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9825
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.026(4)
_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   1.153
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0788P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1684
_reflns_number_gt                1769
_reflns_number_total             3087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja206837j_si_002.cif
_cod_data_source_block           l
_cod_database_code               4106840