Rapid Access to Polyprenylated Phloroglucinols via Alkylative Dearomatization-Annulation: Total Synthesis of (\±)-Clusianone1
Ji Qi; John A. Porco; Journal of the American Chemical Society 129 (2007) 12682–12683; doi:10.1021/ja0762339

data_4110085
_publ_section_title
;
 Rapid Access to Polyprenylated Phloroglucinols via Alkylative
 Dearomatization-Annulation: Total Synthesis of (\+-)-Clusianone1
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12682
_journal_page_last               12683
_journal_paper_doi               10.1021/ja0762339
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C40 H0 Br O9'
_chemical_formula_sum            'C40 H0 Br O9'
_chemical_formula_weight         704.31
_chemical_name_systematic
; 
 ? 
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.325(2)
_cell_angle_beta                 86.301(2)
_cell_angle_gamma                88.173(2)
_cell_formula_units_Z            2
_cell_length_a                   10.8380(5)
_cell_length_b                   11.4593(5)
_cell_length_c                   14.8502(6)
_cell_measurement_reflns_used    8609
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      35.17
_cell_measurement_theta_min      2.30
_cell_volume                     1753.46(13)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            62892
_diffrn_reflns_theta_full        35.63
_diffrn_reflns_theta_max         35.63
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    1.226
_exptl_absorpt_correction_T_max  0.8374
_exptl_absorpt_correction_T_min  0.5791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      0
_exptl_crystal_description       thick
_exptl_crystal_F_000             694
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    isortopic
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         15086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.1897P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                11630
_reflns_number_total             15086
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0762339si20070818_112318.cif
_cod_data_source_block           porco51
_cod_database_code               4110085