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
Full text not available from this repository. (Request a copy)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 |
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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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