Stereoselective Total Synthesis of Serine Palmitoyl-CoA Transferase Inhibitors

Abstract

S e r i n e P a l m i t o y l -C o A T r a n s f e r a s e I n h i b i t o r s HoeAbstract: This review summarizes the total syntheses of the fungal metabolites mycestericin, myriocin, viridiofungin, sulfamisterin, and sphingofungin. The syntheses are organized into three sections: the preparation of (a) the long chain and (b) the polar head group, and (c) the coupling of the two parts of the molecule. The mechanism of action of these potent inhibitors of serine palmitoyl-CoA transferase, the rate-limiting enzyme in the biosynthesis of sphingolipids, is also briefly described.

Recent advances in the total synthesis of polyhydroxylated alkaloids via chiral oxazines

“…Sphingofungins 38–41,126 isolated from fungi, are of significant interest owing to their biological activities as immunosuppressants and potential antifungal agents via the inhibition of serine palmitoyl-CoA transferase (SPT). In addition to sphingofungins, congeners such as myriocin ( M1 , Fig.…”