Synthesis of the Anti‐HIV Agent (−)‐Hyperolactone C by Using Oxonium Ylide Formation–Rearrangement |
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| Authors: | Prof. David M. Hodgson Dr. Stanislav Man |
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| Affiliation: | Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44)?1865‐285002 |
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| 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 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. |
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| Keywords: | hyperolactone oxonium ylide rhodium catalysis sigmatropic rearrangement total synthesis |
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