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Published August 15, 2009 | Supplemental Material
Journal Article Open

An efficient synthesis of the carbocyclic core of zoanthenol


A concise strategy for the synthesis of the carbocyclic portion of zoanthenol is disclosed. The key step involves a 6-endo radical-mediated conjugate addition that constructs the quaternary stereocenter at C(12) and closes the B ring in a stereoselective manner. The synthesis of the C-ring fragment uses an enantioselective desymmetrization to simultaneously establish the absolute stereochemistry of two vicinal quaternary stereocenters. In only 17 steps from known compounds, the route affords an ABC ring system containing all three quaternary stereocenters and appropriate functionality to complete the synthesis of zoanthenol.

Additional Information

© 2009 Elsevier Ltd. Received 18 March 2009; revised 1 May 2009; accepted 8 May 2009. Available online 18 May 2009. The authors wish to thank Novartis (graduate fellowship to J.L.S.), the Philanthropic Education Organization (Scholar Award to J.L.S.), the Fannie and John Hertz Foundation (graduate fellowship to D.C.B.), Abbott, Amgen, Boehringer-Ingelheim, Bristol-Myers Squibb, Merck, and Caltech for their generous financial support. Additionally, we acknowledge Prof. Li Deng of Brandeis University for the kind donation of O-(−)-(menthyl acetate)quinidine and for helpful discussions. Dedicated to Professor Larry E. Overman on the occasion of his receipt of the Tetrahedron Prize.

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