Synthesis of new bicyclic lactam petptidomimetics by ring-closing metathesis reactions (Articolo in rivista)

Type
Label
  • Synthesis of new bicyclic lactam petptidomimetics by ring-closing metathesis reactions (Articolo in rivista) (literal)
Anno
  • 2003-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/S0040-4020(03)00684-7 (literal)
Alternative label
  • Colombo L.; Di Giacomo M.; Vinci V.; Colombo M.; Manzoni L.; Scolastico C. (2003)
    Synthesis of new bicyclic lactam petptidomimetics by ring-closing metathesis reactions
    in Tetrahedron (Oxf., Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Colombo L.; Di Giacomo M.; Vinci V.; Colombo M.; Manzoni L.; Scolastico C. (literal)
Pagina inizio
  • 4501 (literal)
Pagina fine
  • 4513 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 59 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Colombo L.; Di Giacomo M.; Vinci V.; Univ Pavia, Dipartimento Chim Farmaceut, I-27100 Pavia, Italy Colombo M.; Scolastico C.; Università degli Studi di Milano, Dipartimento di Chimica Organica e Industriale, Via Venezian 21, I-20133 Milan, Italy Manzoni L.; CNR - Istituto di Scienze e Tecnologie Molecolari, Via Golgi 19, I-20133 milano, Italy (literal)
Titolo
  • Synthesis of new bicyclic lactam petptidomimetics by ring-closing metathesis reactions (literal)
Abstract
  • An efficient and versatile synthetic method for the preparation of new fused bicyclic lactams 3a and 3b is described. The spirane cyclopentane nucleus was easily installed by diallylation of the pyroglutamate derivative 18 followed by ring-closing metathesis (RCM). A more practical and stereoselective method for the allylation of the alpha-methoxy carbarnate 21, involving the use of InCl3 as a Lewis acid, was developed. In the crucial coupling reaction of the diastereomeric mixture of cis- and trans-pirrolidine derivatives 5a and 5b with N-Cbz vinyl phenylalanine only the cis isomer was found to react. An RCM reaction on the dipeptides 25a and 25b followed by catalytic hydrogenation, gave the final epimeric bicyclic lactams 3a and 3b. The same synthetic sequence on the model compound 7, lacking the spiro cyclopentane nucleus, is also reported. (literal)
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