作者:Lino Colombo、Marcello Di Giacomo、Gloria Brusotti、Nicola Sardone、Mauro Angiolini、Laura Belvisi、Sonia Maffioli、Leonardo Manzoni、Carlo Scolastico
DOI:10.1016/s0040-4020(98)00207-5
日期:1998.5
A flexible stereoselective synthetic scheme was developed to prepare 6,5-fused bicyclic lactams, that molecular mechanics calculations revealed to have a potential as reverse-turn mimetics. The convergence of the synthetic sequence was achieved by attachment of a properly substituted malonate unit to the (2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester, Stereoselective intramolecular alkylation of the malonate afforded the 6-membered lactam fused to the 2-carbalkoxy pyrrolidine nucleus. X-ray diffraction analysis of a more advanced synthetic derivative allowed the unequivocal assignment of the configuration at the newly created quaternary stereocenter as R. (C) 1998 Elsevier Science Ltd. All rights reserved.