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Solid and solution phase synthesis of α-keto amides via azetidinone ring-opening: Application to the synthesis of poststatin

✍ Scribed by Seock-Kyu Khim; John M. Nuss

Book ID
104260877
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
276 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

3,3-Diethoxy-N-sulfonyl and carbamoyl azetidin-2-ones undergo efficient ring-opening reaction with various amine nucleophiles. Subsequent acid hydrolysis of the ketal moiety generated 0t-keto amides in excellent overall yields. The naturally occurring serine protease inhibitor poststatin was synthesized using this ring-opening reaction as the key step.

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