Affiliation:
1. State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic Materials School of Chemistry and Chemical Engineering Nanjing University 163 Xianlin Avenue Nanjing Jiangsu 210023 China
Abstract
AbstractAlkyne‐carbonyl metathesis is a type of carbon‐carbon forming reaction involving the construction a carbon‐carbon double bond and a carbonyl group in one transformation. Herein, a Au(I)‐catalyzed ring‐closing alkyne‐carbonyl metathesis protocol has been developed to make densely substituted γ‐butenolides from propargyl α‐ketoesters. It features 100 % atom economy, excellent substrate flexibility and benign functional group tolerance. Mechanistic studies demonstrate that the coordinative interaction between the gold catalyst and the alkyne might initiate the transfer of an oxygen atom and the formation of the carbon‐carbon double bond. By using this gold‐catalyzed ring‐closing alkyne‐carbonyl metathesis as a key step reaction, four naturally occurring butenolide‐type compounds including decumbic acid (45 % yield for 3 steps), deoxyisosporothric acid (32 % yield for 5 steps), lichesterinic acid (34 % yield for 5 steps) and isomuronic acid (6 % yield for 8 steps) have been synthesized starting from commercially available starting materials.
Funder
National Natural Science Foundation of China
Subject
General Chemistry,Catalysis,Organic Chemistry
Cited by
1 articles.
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