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Synfacts 2008(8): 0787-0787  
DOI: 10.1055/s-2008-1078531
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Pyranicin

Contributor(s): Philip Kocienski, Zofia Komsta
Y. Hattori, S.-i. Furuhata, M. Okajima, H. Konno, M. Abe, H. Miyoshi, T. Goto, H. Makabe*
Shinshu University, Nagano, Japan
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Publication History

Publication Date:
23 July 2008 (online)

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Significance

Pyranicin was isolated from the bark of the Thai tree Goniothalamus giganteus. It is a nanomolar inhibitor of mitochondrial NADH-ubiquinone oxidoreductase (complex I). The key step of the synthesis is the construction of the tetrahydropyran ring in B using a palladium-catalyzed diastereoselective cyclization.