EMAIL THIS PAGE TO A FRIEND

Chemistry (Weinheim an der Bergstrasse, Germany)

Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement.


PMID 21766363

Abstract

Starting from readily available (S)-styrene oxide an asymmetric synthesis is described of the naturally occurring anti-HIV spirolactone (-)-hyperolactone C, which possesses adjacent fully substituted stereocenters. The key step involves a stereocontrolled Rh(II) -catalysed oxonium ylide formation-[2,3] sigmatropic rearrangement of an α-diazo-β-ketoester bearing allylic ether functionality. From the resulting furanone, an acid-catalysed lactonisation and dehydrogenation gives the natural product.