Stereospecific total syntheses of proteasome inhibitors omuralide and lactacystin

Wenxin Gu, Richard B. Silverman*

*Corresponding author for this work

Research output: Contribution to journalArticle

29 Scopus citations

Abstract

Omuralide, a transformation product of the microbial metabolite lactacystin, was the first molecule discovered as a specific inhibitor of the proteasome and is unique in that it specifically inhibits the proteolytic activity of the 20S subunit of the proteasome without inhibiting any other protease activities of the cell. The total syntheses of omuralide and (+)-lactacystin are reported. An important key intermediate is synthesized at an early stage, which allows analogues of these two natural products to be made readily.

Original languageEnglish (US)
Pages (from-to)8287-8293
Number of pages7
JournalJournal of Organic Chemistry
Volume76
Issue number20
DOIs
StatePublished - Oct 21 2011

ASJC Scopus subject areas

  • Organic Chemistry

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