Diastereoselective Synthesis of Bridged Polycyclic Alkaloids via Tandem Acylation/Intramolecular Diels-Alder Reaction
Chih-Hau Chen; Gorakh S. Yellol; Cheng-Hsun Tsai; Prashant B. Dalvi; Chung-Ming Sun; Journal of Organic Chemistry 78 (2013) 9738–9747; doi:10.1021/jo401364s

data_4028630
_publ_section_title
;
 Diastereoselective Synthesis of Bridged Polycyclic Alkaloids via Tandem
 Acylation/Intramolecular Diels-Alder Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9738
_journal_page_last               9747
_journal_paper_doi               10.1021/jo401364s
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C23 H22 N2 O6'
_chemical_formula_sum            'C23 H22 N2 O6'
_chemical_formula_weight         422.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 96.9360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0066(7)
_cell_length_b                   10.7812(6)
_cell_length_c                   17.4741(10)
_cell_measurement_reflns_used    6256
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.000
_cell_measurement_theta_min      2.346
_cell_volume                     2058.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      297(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11249
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.08
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9631
_exptl_absorpt_correction_T_min  0.9354
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0071(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.399
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.399
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0750P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1422
_reflns_number_gt                3396
_reflns_number_total             4037
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401364s_si_002.cif
_cod_data_source_block           tch592m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4028630