Towards the Total Synthesis of Gedunin: Construction of the Fully Elaborated ABC Ring System. Issue 5 (8th March 2017)

• Record Type: Journal Article
• Authors: Pinkerton, David M.; Bernhardt, Paul V.; Savage, G. Paul; Williams, Craig M.
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 5(2017)
• Page Start: 583
• Page End: 597
• Publication Date: 2017-03-08
• Subjects: catalytic hydrogenation -- epoxidation -- gedunin -- natural products -- total synthesis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700013
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: The widely occurring tetranortriterpene natural product gedunin has a well‐established range of important biological properties. Although this molecule has received substantial semi‐synthetic attention from medicinal chemists, it has not received devoted de novo synthetic attention since it was first isolated in 1960. A key feature of the approach presented herein was the decision to utilize a Robinson annulation reaction, which facilitated the installation of the challenging 7‐acetoxy functional group and the completion of the fully functionalized ABC ring system. Abstract : As easy as ABC : Gedunin displays an extraordinary range of biological activities, but, surprisingly, no ground‐up efforts for its synthesis have been reported since the isolation of this limonoid natural product in 1960. This paper provides full details of the first synthesis of the fully functionalized ABC ring system of gedunin.