Short and versatile route to a key intermediate for lactacystin synthesis
Short and versatile route to a key intermediate for lactacystin synthesis
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DOI：
10.1021/ol027387q
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发表时间：
2003-02-06
期刊：
影响因子：
5.2
通讯作者：
Rassias, GA
中科院分区：
文献类型：
--
作者：
Page, PCB;Hamzah, AS;Rassias, GA
通过4步合成了乳酸蛋白酶1的关键中间体14，总产率为33%。关键步骤包括适当功能化的谷氨酸衍生物的环化和随之而来的β -二酮酯体系的烷基化，环α -氨基酮9的c -酰化和12的脱羧苄基化。相关的β， β -二酮酯5与几种亲电试剂也实现了烷基化。
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.