ChemInform Abstract: The Anionic [1,3]-H-Shift Applied in Synthesis: A Novel Access to (+)-Citreoviral

Autor:	Gregor Wille, Johann Mulzer, Joern Bilow
Rok vydání:	2001
Předmět:	chemistry.chemical_compound Allylic rearrangement chemistry Stereochemistry Metabolite Epoxide Citreoviral Stereoselectivity Alcohol General Medicine Combinatorial chemistry Tetrahydrofuran Derivative (chemistry)
Zdroj:	ChemInform. 32
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200116237
Popis:	In this paper we present a highly stereoselective and concise synthesis of the tetrahydrofuran derivative 3 and thus, a formal synthesis of the mycotoxin metabolite (+)-citreoviral (2). In our route we made use of a novel anionic [1,3]-H-shift to convert the homoallylic alcohol 9 into the allylic benzyl ether 10. Another key step was the regio- and stereocontrolled cyclization of epoxide 18b to tetrahydrofuran 19b, which was then converted into ester 3.
Databáze:	OpenAIRE
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