Overcoming synthetic challenges of oridonin a-ring structural diversification: Regio- and stereoselective installation of azides and 1,2,3-triazoles at the c-1, c-2, or c-3 position

Chunyong Ding, Yusong Zhang, Haijun Chen, Christopher Wild, Tianzhi Wang, Mark A. White, Qiang Shen, Jia Zhou

Research output: Contribution to journalArticle

39 Scopus citations

Abstract

Efficient and concise synthetic approaches have been developed for the rapid and diverse installation of azide functionalities at the C-1, C-2, or C-3 positions of oridonin (1) with highly controlled regio- and stereoselectivity, while keeping key reactive pharmacophores intact by utilizing unique preactivation strategies based on the common synthon 4. Further functionalization of these azides through click chemistry yielding triazole derivatives successfully provides access to an expanded natural scaffold-based compound library for potential anticancer agents.

Original languageEnglish (US)
Pages (from-to)3718-3721
Number of pages4
JournalOrganic Letters
Volume15
Issue number14
DOIs
StatePublished - Jul 19 2013

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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