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Synfacts 2008(2): 0122-0122  
DOI: 10.1055/s-2007-992502
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of ()-Frondosin B

Contributor(s): Philip Kocienski, Stewart Eccles
X. Li, T. V. Ovaska*
Connecticut College, New London, USA
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

Frondosin B exhibits anti-HIV, anti-inflammatory, and anti-tumor activity. The authors utilize a microwave-induced 5-exo-dig cyclization (A→B) followed by in situ Claisen rearrangement (B→C) to produce the seven-membered ring. This short synthesis of frondosin B was accomplished in 38% overall yield (7 steps).