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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Abstract

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
Depositing User:	Rachel Smith
Date Deposited:	21 Jun 2011 09:55
Last Modified:	28 Apr 2022 07:35
URI:	https://ueaeprints.uea.ac.uk/id/eprint/32846
DOI:	10.1021/ol027387q

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