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Synfacts 2009(12): 1307-1307  
DOI: 10.1055/s-0029-1218335
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Zoanthamine

Contributor(s): Philip Kocienski
F. Yoshimura, M. Sasaki, I. Hattori, K. Komatsu, M. Sakai, K. Tanino, M. Miyashita*
Hokkaido University, Sapporo, Japan; Kogakuin University, Hachioji, Japan
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Publikationsverlauf

Publikationsdatum:
20. November 2009 (online)

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Significance

Zoanthamine is a marine metabolite that inhibits phorbol myristate-induced inflammation. It is also an analgesic that inhibits human platelet aggregation. Major challenges in this synthesis were (1) construction of the trans-anti-trans perhydrophenanthrene ABC ring system; (2) construction of the three ring C quaternary centers at C9, C12 and C22; (3) construction of the two quaternary aminal centers.