501417-92-1Relevant academic research and scientific papers
Short and versatile route to a key intermediate for lactacystin synthesis.
Bulman Page, Philip C,Hamzah, A Sazali,Leach, David C,Allin, Steven M,Andrews, David M,Rassias, Gerasimos A
, p. 353 - 355 (2003)
[reaction: see text] 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.
