Synthesis of structurally diverse biflavonoids. Issue 38 (20th September 2018)

• Record Type: Journal Article
• Authors: Sum, Tze Jing; Sum, Tze Han; Galloway, Warren R.J.D.; Twigg, David G.; Ciardiello, Joe J.; Spring, David R.
• Is Part Of: Tetrahedron. Volume 74:Issue 38(2018)
• Page Start: 5089
• Page End: 5101
• Publication Date: 2018-09-20
• Subjects: Biflavonoid -- Suzuki-Miyaura cross-coupling -- Methylenation -- Hybrids -- Structural diversity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.05.003
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Synthetic biflavonoids are associated with interesting biological activities, yet they remain poorly explored within drug discovery. Recent years have witnessed a growing interest in synthetic approaches that can provide access to structurally novel biflavonoids so that the biological usefulness of this compound class can be more fully investigated. Herein, we report upon the exploration of strategies based around Suzuki-Miyaura cross-coupling and alcohol methylenation for the synthesis of two classes of biflavonoids: (i) rare 'hybrid' derivatives containing flavonoid monomers belonging to different subclasses, and (ii) homodimeric compounds in which the two flavonoid monomers are linked by a methylenedioxy group. Application of these strategies enabled the preparation of a structurally diverse collection of novel biflavonoids from readily-available starting materials, thereby facilitating the probing of uncharted regions of biologically interesting chemical space. Graphical abstract: Image 1