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Synthesis of (+)-Lyconadin AContributor(s):Steven V. Ley, Philippa B. Cranwell
The University of Tokyo, Japan
Concise Total Synthesis of (+)-Lyconadin A
J. Am. Chem. Soc. 2011, 133: 418-419
18 March 2011 (online)
aza-Prins cyclization - Diels-Alder reaction - electrocyclic ring opening
Lyconadin A was isolated in 2001 from the club moss Lycopodium complanatum and found to exhibit modest biological activity against some cancer cell lines. To date, two total syntheses have been reported by Smith and Sarpong, in 2007 and 2010, respectively.
This highly efficient synthesis contains many notable steps. One particularly interesting transformation is the formation of tetracycle I by ring expansion of the cyclopropane present in G, followed by nucleophilic attack of the secondary amine to quench the allyl cation.