Efficient construction of the A/C/D tricyclic skeleton of palhinine A
Literature Information
Publication Date
2016-07-18
DOI
10.1039/C6QO00222F
Impact Factor
5.281
Authors
Shuangshuang Duan, Dan Long, Changgui Zhao, Gaoyuan Zhao, Ziyun Yuan, Xingang Xie, Jianguo Fang
View Original
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.
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Source Journal
Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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