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Synfacts 2009(3): 0238-0238  
DOI: 10.1055/s-0028-1087700
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of ()-Trichodermamide B

Contributor(s): Philip Kocienski, Stewart Eccles
C.-D. Lu, A. Zakarian*
University of California, Santa Barbara and Florida State University, Tallahassee, USA
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

Trichodermamide B was isolated from a marine-derived fungus Trichoderma virens. Trichodermamide B has good (IC50 0.32 µg mL-¹) in vitro activity against HCT-116 human colon ­carcinoma. The key step in the synthesis is the formation of the oxazine ring in F by a Lewis acid mediated oxaza-Cope rearrangement.