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Titolo:
APPROACHES TO PSEUDOPEPTIDIC ERGOPEPTINES .2. CONSEQUENCES OF THE INCORPORATION OF AN ALPHA-AZAPROLINE RESIDUE INTO THE OXACYCLOLIC SYSTEM
Autore:
PINNEN F; LUISI G; CALCAGNI A; LUCENTE G; GAVUZZO E; CERRINI S;
Indirizzi:
UNIV ROMA LA SAPIENZA,DIPARTIMENTO STUDI FARMACEUT I-00185 ROME ITALY UNIV ROMA LA SAPIENZA,DIPARTIMENTO STUDI FARMACEUT I-00185 ROME ITALY UNIV CATANIA,IST CHIM FARMACEUT I-95125 CATANIA ITALY CNR,IST STRUTTURIST CHIM I-00016 MONTEROTONDO ITALY
Titolo Testata:
Journal of the Chemical Society. Perkin transactions. I
fascicolo: 12, , anno: 1994,
pagine: 1611 - 1617
SICI:
0300-922X(1994):12<1611:ATPE.C>2.0.ZU;2-E
Fonte:
ISI
Lingua:
ENG
Soggetto:
N-ACYL-DIKETOPIPERAZINES; CRYSTAL-STRUCTURE; MOLECULAR-STRUCTURE; PEPTIDE-SYNTHESIS; CONFORMATION; CYCLODEPSITRIPEPTIDES; DIPEPTIDES; ALKALOIDS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
29
Recensione:
Indirizzi per estratti:
Citazione:
F. Pinnen et al., "APPROACHES TO PSEUDOPEPTIDIC ERGOPEPTINES .2. CONSEQUENCES OF THE INCORPORATION OF AN ALPHA-AZAPROLINE RESIDUE INTO THE OXACYCLOLIC SYSTEM", Journal of the Chemical Society. Perkin transactions. I, (12), 1994, pp. 1611-1617

Abstract

As part of a programme to synthesize pseudopeptidic ergopeptines. theintroduction of an alpha-azaproline residue in place of native proline into an ergotamine-like oxacyclolic system has been investigated. Starting material N-[(R)-2-benzyloxypropionyl]cyclo(-Phe-azaPro-) 10 wasprepared following two alternative synthetic routes and was subjectedto reductive O-debenzylation. N,O-Acyl transfer on the resulting N-[(R)-2-hydroxypropionyl] cyclo(Phe-azaPro-) 14 leads, through a new typeof four-heteroatom tetrahedral adduct, to zolidin-1-yl)-carbonyl]ethyl}oxazolidine-2,4-dione 16, as a unique isolable tautomer. Structural and conformational details of compound 14, as revealed by X-ray analysis, are reported and compared with those of previously studied relatedmodels.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 23/09/20 alle ore 09:20:47