Asymmetric Formal Synthesis of (+)-Pyrenolide D

Martin Markovic, Pavol Lopatka, Peter Koóš and Tibor GraczaSynthesis 2014; 46(06): 817-821Publication Date: Jan 1, 2014

A concise, asymmetric formal synthesis of (+)-pyrenolide D from (E)-crotonaldehyde is described. The key steps include an enantioselective Sharpless dihydroxylation of protected hex-4-en-1-yn-3-ol and a highly diastereoselective palladium-catalysed oxycarbonylation of (2R,3S,4S)-hex-5-ene-2,3,4-triol using iron pentacarbonyl as the carbon monoxide source.