Total Synthesis of (\±)-Rocaglamide via Oxidation-Initiated Nazarov Cyclization
John A. Malona; Kevin Cariou; William T. Spencer; Alison J. Frontier; Journal of Organic Chemistry 77 (2012) 1891–1908; doi:10.1021/jo202366c

data_4026969
_publ_section_title
;
 Total Synthesis of (\+-)-Rocaglamide via Oxidation-Initiated Nazarov
 Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1891
_journal_page_last               1908
_journal_paper_doi               10.1021/jo202366c
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C27 H21 F3 O9 S'
_chemical_formula_sum            'C27 H21 F3 O9 S'
_chemical_formula_weight         578.50
_chemical_name_common            frojm09
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.558(3)
_cell_angle_beta                 79.432(3)
_cell_angle_gamma                77.598(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0885(14)
_cell_length_b                   9.8939(15)
_cell_length_c                   14.454(2)
_cell_measurement_reflns_used    2737
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      31.79
_cell_measurement_theta_min      2.50
_cell_volume                     1246.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, \w scans per \f'
_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  0.0779
_diffrn_reflns_av_sigmaI/netI    0.1231
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14383
_diffrn_reflns_theta_full        29.57
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       needle
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         6890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.1319
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0592P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1494
_reflns_number_gt                3660
_reflns_number_total             6890
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202366c_si_004.cif
_cod_data_source_block           frojm09
_cod_database_code               4026969