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Synfacts 2008(2): 0112-0112  
DOI: 10.1055/s-2007-992497
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-cis-Clavicipitic Acid

Contributor(s): Philip Kocienski, Indu Dager
J.-M. Ku, B.-S. Jeong, S.-s. Jew*, H.-g. Park*
Seoul National University and Yeungnam University, Gyeongsan, Korea
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

Isolated from SD58 and Claviceps fusiformis, Clavicipitic acid has a tricyclic azepinoindole skeleton. The key steps in this short and efficient synthesis (10 steps, 20% overall yield) involved an enantioselective phase-transfer-catalyzed alkylation (A→D) and a Pd(II)-catalyzed aminocyclization (G→H).