One-pot double [3 + 2] cycloaddition for diastereoselective synthesis of tetracyclic pyrrolidine compounds
Lu, Qing; Song, Gonghua; Jasinski, Jerry P.; Keeley, Amanda C.; Zhang, Wei; Green Chemistry 14 (2012) 3010–; doi:10.1039/c2gc36066g

data_7208845
_publ_section_title
;
 One-pot double [3 + 2] cycloaddition for diastereoselective synthesis of
 tetracyclic pyrrolidine compounds
;
_journal_issue                   11
_journal_name_full               'Green Chemistry'
_journal_page_first              3010
_journal_paper_doi               10.1039/c2gc36066g
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C25 H25 N3 O8'
_chemical_formula_sum            'C25 H25 N3 O8'
_chemical_formula_weight         495.48
_chemical_name_systematic
;
(3aS,3cS,6aR,7S,9S,9aR)-methyl 2,5-diethyl-7,9-di(furan-2-yl)-
1,3,4,6-tetraoxododecahydro-1H-dipyrrolo[3,4-a:3',4'-f]
pyrrolizine-3b-carboxylate

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0
_cell_angle_beta                 111.566(4)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   10.8016(4)
_cell_length_b                   23.0207(5)
_cell_length_c                   9.9117(3)
_cell_measurement_reflns_used    4165
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.3483
_cell_measurement_theta_min      3.8372
_cell_volume                     2292.11(14)
_computing_cell_refinement       '<i>CrysAlisPRO</i> (Oxford Diffraction, 2010)'
_computing_data_collection       '<i>CrysAlisPRO</i> (Oxford Diffraction, 2010)'
_computing_data_reduction        '<i>CrysAlisRED</i> (Oxford Diffraction, 2010)'
_computing_molecular_graphics    '<i>SHELXTL</i> (Bruker, 2000)'
_computing_publication_material  '<i>SHELXTL</i> (Bruker, 2000)'
_computing_structure_refinement  '<i>SHELXL97</i> (Sheldrick, 2008)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.1500
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11211
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         71.48
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Oxford Diffraction, (2010), CrysAlisPro, Agilent Technologies.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0537
_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^)+(0.0852P)^2^+0.9234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1588
_reflns_number_gt                3402
_reflns_number_total             4254
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2gc36066g.txt
_cod_data_source_block           zhang-2
_cod_original_cell_volume        2292.11(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7208845