Asymmetric total synthesis of cephanolide B. Issue 3 (8th December 2020)

• Record Type: Journal Article
• Authors: Zhang, Hongyuan; He, Haibing; Gao, Shuanhu
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 3(2021)
• Page Start: 555
• Page End: 559
• Publication Date: 2020-12-08
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d0qo01195a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The asymmetric synthesis of cephanolide B, a complex C18 Cephalotaxus dinorditerpenoid, is presented for the first time. Abstract : The asymmetric synthesis of cephanolide B, a complex C18 Cephalotaxus dinorditerpenoid, is presented for the first time. The synthesis relies on the key hexahydrofluorenone core skeleton (A-B-C ring). A remote hydroxyl group directed hydrogenation strategy was developed to selectively reduce the tetra-substituted enone unit. A sequence of modified transformations, including single electron reduction, Barton–McCombie radical deoxygenation, lactonization, and cation mediated Friedel–Crafts cyclization, were efficiently employed to achieve the target.