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Synfacts 2011(4): 0353-0353
DOI: 10.1055/s-0030-1259637
DOI: 10.1055/s-0030-1259637
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (+)-Lyconadin A
Contributor(s):Steven V. Ley, Philippa B. CranwellT. 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
The University of Tokyo, Japan
Concise Total Synthesis of (+)-Lyconadin A
J. Am. Chem. Soc. 2011, 133: 418-419
Further Information
Publication History
Publication Date:
18 March 2011 (online)
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.