Asymmetric synthesis of (−)-tetrahydrolipstatin

Attempts toward the asymmetric synthesis of (−)-tetrahydrolipstatin are described. A palladium catalyzed Wacker-type reaction to convert an alkene to a ketone, highly diastereoselective reduction of a β-hydroxy ketone, selective oxidation of a diol, and modular synthesis are the key features of the successful approach.

Graphical abstractDownload full-size image A palladium catalyzed Wacker-type reaction, highly diastereoselective reduction of a β-hydroxy ketone, selective oxidation of a diol, and modular approach constitute the key features of the successful route to THL. Attempts at introducing the decyl chain employing an ene reaction failed.