Iron‐Catalyzed Synthesis of the Hexahydrocyclopenta[c]furan Core and Concise Total Synthesis of Polyflavanostilbene B. (16th July 2018)

• Record Type: Journal Article
• Authors: Wang, Xujie; Liu, Fu; Yun, Juping; Feng, Ziming; Jiang, Jianshuang; Yang, Yanan; Zhang, Peicheng
• Is Part Of: Angewandte Chemie. Volume 130:Number 32(2018)
• Page Start: 10284
• Page End: 10288
• Publication Date: 2018-07-16
• Subjects: Eisen -- Naturstoffsynthese -- Radikalische Cyclisierungen -- Spiroverbindungen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201804329
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The first synthesis of polyflavanostilbene B (1 ), which has seven contiguous stereocenters including two quaternary carbon centers, from abundant polymeric (−)‐epicatechin gallate on a gram scale in three steps without the use of protecting groups is reported. The key transformations of this strategy include a regioselective and stereoselective substitution of resveratrol to give the 4‐derivative of (−)‐epicatechin 3‐gallate and an iron‐catalyzed cyclization reaction. The possible radical cyclization mechanism in the formation of the hexahydrocyclopenta[c]furan core is also discussed.