Total Synthesis of (+)‐Scyphostatin, a Potent and Specific Inhibitor of Neutral Sphingomyelinase

Abstract

The five crucial steps in the first total synthesis of (+)-scyphostatin from D-arabinose involve (see picture): a) stereoselective aldol coupling to form a quaternary stereocenter, b) ring-closing metathesis (RCM) to construct the cyclohexene ring, c) Negishi coupling for the preparation of the fatty acid side chain, d) amide formation to connect the cyclohexene and fatty acid segments, e) stereospecific epoxide-ring formation. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z54192_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.