Divergent Synthesis and Chemical Reactivity of Bicyclic Lactone Fragments of Complex Rearranged Spongian Diterpenes
Martin J. Schnermann; Christopher M. Beaudry; Nathan E. Genung; Stephen M. Canham; Nicholas L. Untiedt; Breanne D. W. Karanikolas; Christine Sütterlin; Larry E. Overman; Journal of the American Chemical Society 133 (2011) 17494–17503; doi:10.1021/ja207727h

data_4107036
_publ_section_title
;
 Divergent Synthesis and Chemical Reactivity of Bicyclic Lactone Fragments
 of Complex Rearranged Spongian Diterpenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17494
_journal_page_last               17503
_journal_paper_doi               10.1021/ja207727h
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_sum            'C20 H23 F3 O6'
_chemical_formula_weight         416.38
_space_group_IT_number           146
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            9
_cell_length_a                   26.422(7)
_cell_length_b                   26.422(7)
_cell_length_c                   7.967(2)
_cell_measurement_reflns_used    3119
_cell_measurement_temperature    88(2)
_cell_measurement_theta_max      22.34
_cell_measurement_theta_min      2.67
_cell_volume                     4817(2)
_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      88(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17525
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       needle
_exptl_crystal_F_000             1962
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4383
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0400P)^2^+0.1660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0866
_reflns_number_gt                3373
_reflns_number_total             4383
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja207727h_si_002.cif
_cod_data_source_block           leo247
_cod_original_cell_volume        4816(2)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               4107036