1334180-37-8Relevant articles and documents
Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement
Hodgson, David M.,Man, Stanislav
, p. 9731 - 9737 (2011/10/05)
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 RhII-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.