333302-67-3Relevant academic research and scientific papers
The Anionic [1,3]-H-Shift Applied in Synthesis: A Novel Access to (+)-Citreoviral
Mulzer, Johann,Bilow, Joern,Wille, Gregor
, p. 773 - 778 (2007/10/03)
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 stereo-controlled cyclization of epoxide 18b to tetrahydrofuran 19b, which was then converted into ester 3.
