Total Synthesis of ent-Dioxepandehydrothyrsiferol via a Bromonium-Initiated Epoxide-Opening Cascade
Jessica Tanuwidjaja; Sze-Sze Ng; Timothy F. Jamison; Journal of the American Chemical Society 131 (2009) 12084–12085; doi:10.1021/ja9052366

data_4104949
_publ_section_title
;
 Total Synthesis of ent-Dioxepandehydrothyrsiferol via a
 Bromonium-Initiated Epoxide-Opening Cascade
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12084
_journal_page_last               12085
_journal_paper_doi               10.1021/ja9052366
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H33 Br O6'
_chemical_formula_weight         461.38
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5972(11)
_cell_length_b                   13.1485(13)
_cell_length_c                   16.0477(16)
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.29
_cell_measurement_theta_min      2.47
_cell_volume                     2236.0(4)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2008)'
_computing_data_collection       'APEX2 3.0 (Bruker-AXS, 2008)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2008)'
_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      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'omega and phi 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  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            60558
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    1.871
_exptl_absorpt_correction_T_max  0.7060
_exptl_absorpt_correction_T_min  0.5773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         6525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0508P)^2^+0.1627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                5821
_reflns_number_total             6525
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9052366_si_002.cif
_cod_data_source_block           08351
_cod_database_code               4104949