Total Synthesis and Structural Revision of the Piperarborenines via Sequential Cyclobutane C-H Arylation
Will R. Gutekunst; Phil S. Baran; Journal of the American Chemical Society 133 (2011) 19076–19079; doi:10.1021/ja209205x

data_4107175
_publ_section_title
;
 Total Synthesis and Structural Revision of the Piperarborenines via
 Sequential Cyclobutane C-H Arylation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19076
_journal_page_last               19079
_journal_paper_doi               10.1021/ja209205x
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C36 H43 N O10 S'
_chemical_formula_weight         681.77
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 100.566(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.0063(5)
_cell_length_b                   9.0198(3)
_cell_length_c                   20.7729(6)
_cell_measurement_reflns_used    7072
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.35
_cell_measurement_theta_min      2.47
_cell_volume                     3500.78(18)
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27418
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.56
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       plate
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.096
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         6536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0775
_refine_ls_shift/su_max          0.059
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1300P)^2^+3.6000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2103
_refine_ls_wR_factor_ref         0.2474
_reflns_number_gt                4075
_reflns_number_total             6536
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja209205x_si_004.cif
_cod_data_source_block           baran213
_cod_database_code               4107175