Stereoselective Synthesis of Tabtoxinine-beta-lactam by Using the Vinylogous Mukaiyama Aldol Reaction with Acetate-Type Vinylketene Silyl N,O-Acetal and alpha-Keto-beta-lactam

摘要

Stereoselective total synthesis of tabtoxinine-beta-lactam has been achieved. The vinylogous Mukaiyama aldol reaction with vinylketene silyl N,O-acetal and alpha-keto-beta-lactam proceeded to afford the adduct possessing a T beta L-skeleton with a tert-alcohol in high yield and stereoselectivity. Stereoselective introduction of the amino group has been accomplished by azidation at the alpha position of the imide followed by hydrogenolysis. A straightforward method to achieve the potent inhibitor of glutamine synthetase, possessing both alpha-hydroxy-beta-lactam and alpha-amino acid moieties, has been established.