New and Expeditious Tandem Sequence Aza-Michael/Intramolecular Nucleophilic Substitution Route to Substituted γ-Lactams: Synthesis of the Tricyclic Core of (±)-Martinellines
Sébastien Comesse; Morgane Sanselme; Adam Daïch; Journal of Organic Chemistry 73 (2008) 5566–5569; doi:10.1021/jo702752w

data_4023525
_publ_section_title
;
 New and Expeditious Tandem Sequence Aza-Michael/Intramolecular
 Nucleophilic Substitution Route to Substituted \g-Lactams:
 Synthesis of the Tricyclic Core of (+-)-Martinellines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5566
_journal_page_last               5569
_journal_paper_doi               10.1021/jo702752w
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C21 H20 N2 O4'
_chemical_formula_sum            'C21 H20 N2 O4'
_chemical_formula_weight         364.39
_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                 96.135(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.601(2)
_cell_length_b                   9.2080(10)
_cell_length_c                   17.816(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1892.2(5)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14534
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0766P)^2^+0.3575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1367
_reflns_number_gt                3245
_reflns_number_total             3883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702752w-File001.cif
_cod_data_source_block           sc422m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023525