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Synfacts 2007(5): 0458-0458  
DOI: 10.1055/s-2007-968388
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Cladiella-6,11-dien-3-ol

Contributor(s): Philip Kocienski, Thomas Snaddon
H. Kim, H. Lee, J. Kim, S. Kim, D. Kim*
Seoul National University, Korea
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Publication History

Publication Date:
24 April 2007 (online)

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Significance

The cladiellin diterpenes are cembranoid natural products containing an oxatri­cyclic core. Both C6-olefin isomers are known in nature and these syntheses represent the first approach to a (6E)-configured member. Key to this effort is a diastereoselective intramolecular Diels-Alder reaction to install the fused five-six-ring system. For an approach to a (6Z)-cladiellin diterpene using an intramolecular Diels-Alder reaction, see: M. J. Crimmins, J. M. Ellis J. Am. Chem. Soc. 2005 127, 17200-17201.