hide
Free keywords:
enzymatic resolution; natural products synthesis; ruthenium; sphingolipids; trans-hydrogenation
Abstract:
A scalable approach to (2R)-hydroxyoctadec-3-enoic acid ((−)-2) is reported, which is the fatty acid constituent of numerous sphingolipids of biological significance. Key to success was the chemoselective trans-hydrogenation of a functionalized propargylic alcohol precursor with [Cp*RuCl]4 as the catalyst, followed by lipase-catalyzed resolution of the racemic product. (−)-2 then served the shortest total synthesis of the marine natural product symbioramide known to date.
