Biomimetic type approach to the tricyclic core of xyloketals. Application to a short, stereocontrolled synthesis of alboatrin and first synthesis of xyloketal G

D Sarkar, RV Venkateswaran

Index: Sarkar, Debayan; Venkateswaran, Ramanathapuram V. Tetrahedron, 2011 , vol. 67, # 25 p. 4559 - 4568

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Citation Number: 6

Abstract

Abstract A convenient approach to the linear tetrahydrofurano benzopyran ring system of xyloketals is described. An orthoester Claisen rearrangement of a chromenol and an intra- molecular cationic cyclization are the key steps in the synthesis. A short, stereocontrolled and high yield synthesis of the phytotoxic metabolite alboatrin was achieved employing this strategy. A unique case of Lewis acid catalyzed isomerization of epi-alboatrin to alboatrin ...