A Convergent and Stereocontrolled Cycloaddition Strategy toward Eudesmane Sesquiterpenoid: Total Synthesis of (\±)-6β,14-Epoxyeudesm-4(15)-en-1β-ol
Cui-Cui Wang; Wei-Dong Z. Li; Journal of Organic Chemistry 77 (2012) 4217–4225; doi:10.1021/jo300556r

data_4027187
_publ_section_title
;
 A Convergent and Stereocontrolled Cycloaddition Strategy toward Eudesmane
 Sesquiterpenoid: Total Synthesis of
 (\+-)-6\b,14-Epoxyeudesm-4(15)-en-1\b-ol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4217
_journal_page_last               4225
_journal_paper_doi               10.1021/jo300556r
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C16 H25 F O3'
_chemical_formula_weight         284.36
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.476(4)
_cell_angle_beta                 80.638(4)
_cell_angle_gamma                77.042(4)
_cell_formula_units_Z            2
_cell_length_a                   7.924(3)
_cell_length_b                   9.569(4)
_cell_length_c                   13.406(5)
_cell_measurement_reflns_used    1427
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.38
_cell_measurement_theta_min      2.42
_cell_volume                     948.8(6)
_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 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5873
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.995
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_platon_squeeze_details
;
;
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.020(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   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0766P)^2^+0.0061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                2244
_reflns_number_total             3451
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300556r_si_005.cif
_cod_data_source_block           p-1
_cod_original_cell_volume        948.8(7)
_cod_database_code               4027187