Asymmetric total synthesis strategies of halichlorine and pinnaic acid

Abstract

Halichlorine and pinnaic acid are structurally related natural alkaloids isolated from different marine organisms. These two marine alkaloids bearing a 6-azaspiro[4.5]decane skeleton demonstrate a wide range of biological effects. It is this kind of unique structure and potentially valuable biological activity that have prompted strong synthetic interest, making it a research focus in recent years. Since the first total synthesis of halichlorine and pinnaic acid completed by Danishefsky's group, many groups have reported their outstanding synthesis methods especially the asymmetric synthesis strategies. This review summarizes the asymmetric synthesis strategies of halichlorine and pinnaic acid using a 6-azaspiro[4.5]decane skeleton as the key intermediate, which can provide some guidance for related work.