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Gold(I)‐Catalyzed Tandem Transformation with Diynes: Rapid Access to Linear Cyclopentenone‐Fused Polycyclic Molecules
Author(s) -
Yu Congjun,
Chen Bin,
Zhou Tian,
Tian Qingshan,
Zhang Guozhu
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201503599
Subject(s) - cyclopentenone , tandem , combinatorial chemistry , chemistry , catalysis , ring (chemistry) , molecule , transformation (genetics) , stereochemistry , organic chemistry , materials science , biochemistry , composite material , gene
An efficient and convenient synthesis of useful linear cyclopentenone‐fused polycyclic compounds has been achieved through a novel gold(I)‐catalyzed transformation of diynes. The method demonstrates high product yields and tolerates of a wide variety of important functional groups. Gold‐vinylidene formation, methoxy group migration, and Nazarov‐type cyclization are proposed to be the key steps in the reaction pathway. The synthetic utility of this method is demonstrated by converting the product to eight‐membered‐ring‐fused compound.