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Synfacts 2006(2): 0100-0100  
DOI: 10.1055/s-2005-923600
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Rollimembrin

Contributor(s): Philip Kocienski, Fiona Black
G. Keum, C. H. Hwang, S. B. Kang, Y. Kim, E. Lee*
Seoul National University, Korea
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

Rolliniastatin 1, Rollimembrin, and Membranacin are Annonaceous acetogenins isolated from Rollinia membranacea and Rollinia mucosa. They are in vitro inhibitors of the mitochondrial respiratory chain complex I. The dihydroxy bis-oxolane core of these natural products was constructed with high diastereoselectivity by two radical cyclization-Pummerer rearrangement-allylation sequences.