Efficient construction of the A/C/D tricyclic skeleton of palhinine A. Issue 9 (28th July 2016)

• Record Type: Journal Article
• Authors: Duan, Shuangshuang; Long, Dan; Zhao, Changgui; Zhao, Gaoyuan; Yuan, Ziyun; Xie, Xingang; Fang, Jianguo; She, Xuegong
• Is Part Of: Organic chemistry frontiers. Volume 3:Issue 9(2016:Sep.)
• Page Start: 1137
• Page End: 1143
• Publication Date: 2016-07-28
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c6qo00222f
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : An efficient approach for the synthesis of the 9/6/6 tricyclic structure of Lycopodium alkaloid palhinine A has been accomplished. This protocol can undergo ring constriction to rapidly construct the highly strained nine-membered azonane ring of palhinine A. Abstract : An efficient approach for the synthesis of the 9/6/6 tricyclic structure of Lycopodium alkaloid palhinine A has been accomplished. The developed synthetic route features oxidative dearomatization and tandem hydroxyl oxidation/intramolecular Diels–Alder (IMDA) reactions to assemble the A/C/D tricyclic ring system. Most importantly, the protocol can undergo ring constriction to rapidly construct the highly strained nine-membered azonane ring of palhinine A.