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

• DOI: 10.1021/acs.orglett.7b00814
• Publication Date: 2017-05-04T13:06:26Z
• Authors: Hirotaka Ejima; Fumihiro Wakita; Ryo Imamura; Takuya Kato; Seijiro Hosokawa
• Keywords: Aldol reaction; Lactam; Imide; Hydrogenolysis

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