Bibliographic Details
| Title: |
Stereoselective Synthesis of Tabtoxinine-β-lactam by Using the Vinylogous Mukaiyama Aldol Reaction with Acetate-Type Vinylketene SilylN,O-Acetal and α-Keto-β-lactam. |
| Authors: |
Hirotaka Ejima1, Fumihiro Wakita1, Ryo Imamura1, Takuya Kato1, Seijiro Hosokawa1 seijiro@waseda.jp |
| Source: |
Organic Letters. May2017, Vol. 19 Issue 10, p2530-2532. 1p. |
| Subject Terms: |
*TABTOXIN, *LACTAMS, *STEREOSELECTIVE reactions, *ALDOLS, *IMIDES |
| Abstract: |
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 with a tert-alcohol in high yield and stereoselectivity. Stereoselective introduction of the amino group has been accomplished by azidation at the α position of the imide followed by hydrogenolysis. A straightforward method to achieve the potent inhibitor of glutamine synthetase, possessing both α-hydroxy-β-lactam and α-amino acid moieties, has been established. [ABSTRACT FROM AUTHOR] |
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| Database: |
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