Total Syntheses of Myriocin, Mycestericins and Sphingofungin E: Sphingosine Analogues Containing a β, β′-Dihydroxy α-Amino Acid Framework

Abstract

Natural sphingosine analogues containing a β, β′-dihydroxy α-amino acid framework demonstrate potent antifungal or immunosuppressive activity and are potential candidates for the development of chemical tools or pharmaceuticals. This Highlight Review presents the total syntheses of sphingosine analogues, myriocin, mycestericins and sphingofungin E, focusing on the strategies used for stereoselective construction of the quaternary α-amino acid motif embedded in these sphingosine analogues. Various methods have been developed, including C–C/C–N bond formation and desymmetrization strategies, leading to the development of efficient and divergent synthetic routes.