Cyclopropene cycloadditions with annulated furans: total synthesis of (+)- and (-)-frondosin B and (+)-frondosin a.
Oblak, E. Zachary; Vanheyst, Michael D.; Li, Jin; Wiemer, Andrew J.; Wright, Dennis L.; Journal of the American Chemical Society 136 (2014) 4309–4315; doi:10.1021/ja413106t

data_4121457
_publ_section_title
;
 Cyclopropene cycloadditions with annulated furans: total synthesis of
 (+)- and (-)-frondosin B and (+)-frondosin a.
;
_journal_issue                   11
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4309
_journal_page_last               4315
_journal_paper_doi               10.1021/ja413106t
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Br2 O3 C11 H10'
_chemical_formula_sum            'C11 H10 Br2 O3'
_chemical_formula_weight         350.01
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.547(14)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   7.0876(17)
_cell_length_b                   8.3046(19)
_cell_length_c                   10.113(2)
_cell_measurement_reflns_used    5358
_cell_measurement_temperature    223
_cell_measurement_theta_max      27.68
_cell_measurement_theta_min      3.05
_cell_volume                     560.9(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD (SCX mini)'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5811
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.234
_exptl_absorpt_correction_T_max  0.561
_exptl_absorpt_correction_T_min  0.313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340.00
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.010
_refine_diff_density_min         -0.530
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1177 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.056(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2545
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0240P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                2069
_reflns_number_total             2545
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja413106t_si_002.cif
_cod_data_source_block           '_zo02'
_cod_original_formula_sum        'Br2 O3 C11 H10'
_cod_database_code               4121457