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_4026967
_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         'C26 H22 O6'
_chemical_formula_sum            'C26 H22 O6'
_chemical_formula_weight         430.44
_chemical_name_common            frojm06
_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                 96.663(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3933(12)
_cell_length_b                   9.5780(10)
_cell_length_c                   20.154(2)
_cell_measurement_reflns_used    4067
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      32.17
_cell_measurement_theta_min      2.36
_cell_volume                     2184.5(4)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0759
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            29761
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         5414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0329P)^2^+0.8404P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                3535
_reflns_number_total             5414
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202366c_si_002.cif
_cod_data_source_block           frojm06
_cod_original_cell_volume        2184.4(4)
_cod_database_code               4026967