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 White, Qiang Shen, Jia Zhou

Research output: Contribution to journalArticle

35 Citations (Scopus)

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

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Triazoles
Azides
installing
Click Chemistry
chemistry
Stereoselectivity
Regioselectivity
rings
Scaffolds
Antineoplastic Agents
Libraries
Derivatives
oridonin

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

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

In: Organic Letters, Vol. 15, No. 14, 19.07.2013, p. 3718-3721.

Research output: Contribution to journalArticle

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