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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...
The first total synthesis of (-)-xialenon A was achieved via enantioselective transannular desymmetrisation of a substituted cycloctene oxide using an organolithium/(-)-α-isosparteine combination. Oxidation of the resulting bicyclo[3.3.0]octanol gave an enone which underwent stereoselective conjugate allylation; subsequent α'-hydroxylation on the more hindered face of a derived enone using hypervalent...
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