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Titolo:
Stereoselective preparation of protected thymine polyoxin C and approachestowards synthesis of its C2 '-modified analogues
Autore:
Dehoux, C; Gorrichon, L; Baltas, M;
Indirizzi:
Univ Toulouse 3, CNRS, UMR 5068, F-31062 Toulouse 04, France Univ Toulouse3 Toulouse France 04 UMR 5068, F-31062 Toulouse 04, France
Titolo Testata:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 6, , anno: 2001,
pagine: 1105 - 1113
SICI:
1434-193X(200103):6<1105:SPOPTP>2.0.ZU;2-E
Fonte:
ISI
Lingua:
ENG
Soggetto:
CANDIDA-ALBICANS; OXIDATION; AGENTS; NUCLEOSIDES; VERSATILE; PRECURSOR; ALCOHOLS; SUGAR;
Keywords:
antifungal agents; azidolactone; fluorine; polyoxin;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
49
Recensione:
Indirizzi per estratti:
Indirizzo: Baltas, M Univ Toulouse 3, CNRS, UMR 5068, 118 Route Narbonne, F-31062 Toulouse 04, France Univ Toulouse 3 118 Route Narbonne Toulouse France 04 4, France
Citazione:
C. Dehoux et al., "Stereoselective preparation of protected thymine polyoxin C and approachestowards synthesis of its C2 '-modified analogues", EUR J ORG C, (6), 2001, pp. 1105-1113

Abstract

Polyoxins form an important class of pyrimidine peptide antifungal agents. The preparation of thymine polyoxin C, which is the nucleosidic component of some polyoxins, is reported, together with attempts to synthesize C2'-fluoro analogues. Epimeric 3-hydroxyazidolactones 2a and 2b, obtained from diastereoisomeric epoxy hydroxy esters, were dehydrated to afford butenolide 3. Dihydroxylation and further functional manipulation yielded thymine polyoxin C. Attempts to form the 2,2'-anhydronucleoside and to direct nucleophilic fluorination with DAST on a monoprotected nucleoside were unsuccessful. Electrophilic fluorination of azidolactone with NFSI permitted the formation of an alpha -fluorolactone, which is an interesting intermediate for thepreparation of a C2'-fluoro analogue.

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Documento generato il 05/04/20 alle ore 13:31:48