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Synfacts 2011(4): 0353-0353  
DOI: 10.1055/s-0030-1259637
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Lyconadin A

Rezensent(en):Steven V. Ley, Philippa B. Cranwell
T. Nishimura, A. K. Unni, S. Yokoshima, T. Fukuyama*
The University of Tokyo, Japan
Concise Total Synthesis of (+)-Lyconadin A
J. Am. Chem. Soc.  2011,  133:  418-419  
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Publikationsverlauf

Publikationsdatum:
18. März 2011 (online)

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Key words

aza-Prins cyclization - Diels-Alder reaction - electrocyclic ring opening

Significance

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.

Comment

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.

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