Divergent and concise total syntheses of dihydrochalcones and 5-deoxyflavones recently isolated from Tacca species and Mimosa diplotricha. Issue 26 (1st July 2015)

• Record Type: Journal Article
• Authors: Sum, Tze Han; Sum, Tze Jing; Stokes, Jamie E.; Galloway, Warren R.J.D.; Spring, David R.
• Is Part Of: Tetrahedron. Volume 71:Issue 26/27(2015)
• Page Start: 4557
• Page End: 4564
• Publication Date: 2015-07-01
• Subjects: Natural product synthesis -- Flavonoids -- Dihydrochalcones -- Deoxyflavones -- Divergent synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.02.017
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Dihydrochalcones and 5-deoxyflavones are types of compounds possessing various biologically interesting properties. Herein, we report the concise and divergent total syntheses of several naturally occurring dihydrochalcones and 5-deoxyflavones from readily available starting materials. The divergent strategy is based around manipulation of a common chalcone scaffold and features application of Algar–Flynn–Oyamada oxidation and benzoquinone C–H activation methodologies. These are the first reported total syntheses of these biologically interesting compounds and the concise and flexible route should be readily amenable to future analogue generation. Furthermore, this work provides an illustration of the utility of divergent synthesis for the expedient and step-economical preparation of natural product libraries. Graphical abstract: