Brønsted acid assisted activation of imide carbonyl group: regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine.
Selvakumar, Jayaraman; Ramanathan, Chinnasamy Ramaraj; Organic & biomolecular chemistry 9 (2011) 7643–7646; doi:10.1039/c1ob06349a

data_7152067
_publ_section_title
;
 Br\/onsted acid assisted activation of imide carbonyl group:
 regioselective synthesis of isoindoloisoquinolinone alkaloid
 (+-)-nuevamine.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7643
_journal_page_last               7646
_journal_paper_doi               10.1039/c1ob06349a
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C20 H21 N O6'
_chemical_formula_weight         371.38
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_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                90.00
_cell_angle_beta                 95.344(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1550(2)
_cell_length_b                   19.4043(5)
_cell_length_c                   9.8299(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1928.57(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15615
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.095
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3380
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.5041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                2591
_reflns_number_total             3380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06349a.txt
_cod_data_source_block           crr-66-crr-226
_cod_database_code               7152067