Premium
Iron‐Catalyzed Synthesis of the Hexahydrocyclopenta[ c ]furan Core and Concise Total Synthesis of Polyflavanostilbene B
Author(s) -
Wang Xujie,
Liu Fu,
Yun Juping,
Feng Ziming,
Jiang Jianshuang,
Yang Yanan,
Zhang Peicheng
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201804329
Subject(s) - stereocenter , chemistry , regioselectivity , furan , catalysis , derivative (finance) , stereoselectivity , stereochemistry , gallate , combinatorial chemistry , total synthesis , enantioselective synthesis , organic chemistry , financial economics , economics , nuclear chemistry
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.