An efficient and convenient approach to the total synthesis of sphingofungin.
As a new member of the sphingofungin family, sphingofungin F exhibits interesting physiological activities with a structural unit of an alpha-substituted alanine. Described herein is an efficient and convenient stereoselective synthesis of sphingofungin F from L-(+)-tartaric acid, which utilizes Sharpless asymmetric epoxidation of allylic alcohol and Lewis acid-catalyzed intramolecular epoxide-opening reaction with an N-nucleophile, to introduce the other two desired stereogenic centers. Side chain functionality was incorporated into the chiral segment using a Wittig reaction.
Liu
D G
DG
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, China.
Wang
B
B
Lin
G Q
GQ
D000596:Amino Acids / Q000138:chemical synthesis; D002384:Catalysis; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy
D000596:Amino Acids; D005231:Fatty Acids, Unsaturated; C078944:sphingofungin F