title: 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.
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.
authors.affiliation: Chemical Biology Program, Department of Pharmacology and Toxicology, University of Texas Medical Branch, Galveston, Texas 77555, USA.
authors.forename: Chunyong
authors.initials: C
authors.lastname: Ding
authors.forename: Yusong
authors.initials: Y
authors.lastname: Zhang
authors.forename: Haijun
authors.initials: H
authors.lastname: Chen
authors.forename: Christopher
authors.initials: C
authors.lastname: Wild
authors.forename: Tianzhi
authors.initials: T
authors.lastname: Wang
authors.forename: Mark A
authors.initials: MA
authors.lastname: White
authors.forename: Qiang
authors.initials: Q
authors.lastname: Shen
authors.forename: Jia
authors.initials: J
authors.lastname: Zhou
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D045786:Diterpenes, Kaurane / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D001386:Azides; D045786:Diterpenes, Kaurane; D014230:Triazoles; C011959:oridonin