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

Autor:	Johann Mulzer, Joern Bilow, Gregor Wille
Rok vydání:	2000
Předmět:	chemistry.chemical_compound Allylic rearrangement Chemistry Metabolite Epoxide Citreoviral Alcohol Stereoselectivity Combinatorial chemistry Tetrahydrofuran Derivative (chemistry)
Zdroj:	Journal für praktische Chemie. 342:773-778
ISSN:	1521-3897 1436-9966
DOI:	10.1002/1521-3897(200010)342:8<773::aid-prac773>3.0.co;2-w
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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