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Synfacts 2007(3): 0232-0232  
DOI: 10.1055/s-2007-968201
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Antheliolide A

Contributor(s): Philip Kocienski, Thomas Snaddon
C. S. Mushti, J.-H. Kim, E. J. Corey*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

The absolute stereochemistry of antheliolide A, a complex sesterterpenoid isolated from Anthelica glauca, was determied by a remarkable synthesis featuring (a) a diastereoselective intramolecular ketene [2+2] cycloaddition giving a bicyclo[3.2.0]heptanone, (b) the preparation of a β-keto sulfone by the Pd-catalyzed [2,3]-sigmatropic rearrangement of a propargylic benzenesulfinate ester, and (c) annulation by the intramolecular union of a β-keto sulfone pro-nucleophile and a Pd-π-allyl system.