The anionic [1,3]-H-shift applied in synthesis: A novel access to (+)-citreoviral

In this paper we present a highly stereoselective and concise synthesis of the tetrahydrofuran derivative 3 and thus, a formal synthesis of the mycoto xin metabolite (+)-citreoviral (2). In our route we made use of a novel ani onic [1,3]-H-shift to convert the homoallylic alcohol 9 into the allylic be nzyl ether 10. Another key step was the regio- and stereocontrolled cycliza tion of epoxide 18b to tetrahydrofuran 19b, which was then converted into e ster 3.