Facile synthesis of norwogonin, isoscutellarein, and herbacetin. Issue 30 (27th July 2016)

• Record Type: Journal Article
• Authors: Yuan, Hu; Ye, Ji; Chen, Hao; Zhao, Zeng; Luo, Xukai; Zhang, Weidong; Sun, Qingyan
• Is Part Of: Tetrahedron letters. Volume 57:Issue 30(2016)
• Page Start: 3389
• Page End: 3391
• Publication Date: 2016-07-27
• Subjects: 5, 7, 8-Trihydroxyflavone -- Synthesis -- Borylation -- Oxidation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.06.085
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A new approach to 5, 7, 8-trihydroxyflavones is provided. Satisfactory yields of norwogonin, isoscutellarein, and herbacetin are obtained. Borylation of sterically hindered aryl iodides is developed. No column chromatography is needed for purification. Abstract: An expeditious synthesis of norwogonin, isoscutellarein, and herbacetin, has been accomplished by a strategy featuring a borylation of sterically hindered aryl iodide and a one-pot oxidation to generate the C-3 and C-8 OH groups. The total synthesis gives excellent yields and conventional flash column chromatography is not needed for purification.