Short and versatile route to a key intermediate for lactacystin synthesis

Bulman Page, Philip C. B., Hamzah, A. Sazali, Leach, David C., Allin, Steven M., Andrews, David M. and Rassias, Gerasimos A. (2003) Short and versatile route to a key intermediate for lactacystin synthesis. Organic Letters, 5 (3). pp. 353-355. ISSN 1523-7060

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A key intermediate 14 for the synthesis of lactacystin 1 has been constructed in four steps and 33% overall yield. The key steps involve cyclization of a suitably functionalized glutamic acid derivative and concomitant alkylation of the resulting beta,beta-diketoester system, C-acylation of the cyclic alpha-amidoketone 9, and decarboxylbenzylation of 12. Alkylation of a related beta,beta-diketoester 5 was additionally achieved with several electrophiles.

Item Type: Article
Uncontrolled Keywords: proteasome function,analogs,d-glucose,efficient,beta-lactone,inhibition,(+)-lactacystin
Faculty \ School: Faculty of Science > School of Chemistry
UEA Research Groups: Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017)
Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User: Rachel Smith
Date Deposited: 21 Jun 2011 09:55
Last Modified: 24 Oct 2022 02:53
DOI: 10.1021/ol027387q

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