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ARS Home » Midwest Area » Madison, Wisconsin » U.S. Dairy Forage Research Center » Dairy Forage Research » Research » Publications at this Location » Publication #346296

Research Project: Redesigning Forage Genetics, Management, and Harvesting for Efficiency, Profit, and Sustainability in Dairy and Bioenergy Production Systems

Location: Dairy Forage Research

Title: Synthesis of nepetoidin B

item TIMOKHIN, VITALIY - University Of Wisconsin
item REGNER, MATTHEW - University Of Wisconsin
item TSUJI, YUKIKO - University Of Wisconsin
item Grabber, John
item RALPH, JOHN - University Of Wisconsin

Submitted to: Synlett
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 2/26/2018
Publication Date: 3/8/2018
Citation: Timokhin, V.I., Regner, M., Tsuji, Y., Grabber, J.H., Ralph, J. 2018. Synthesis of nepetoidin B. Synlett. A-C 29(9):1229-1231. doi: 10.1055/s-0036-1591556.

Interpretive Summary: Nepetoidin B is a natural plant product having antibacterial, antifungal, and free radical scavenging properties that make it potentially valuable for medicinal uses and other applications. It can be isolated only in very small quantities from some plant species. This paper describes the first reported laboratory synthesis of nepetoidin B.

Technical Abstract: The total synthesis of nepetoidin B (the 2-(3,4-dihydroxyphenyl)ethenyl ester of 3-(3,4-dihydroxy¬phenyl)-2-propenoic acid) has been achieved in two steps from commercially available 1,5-bis(3,4-dimethoxyphenyl)-1,4-pentadien-3-one. Tetramethylated nepetoidin B was prepared directly by Baeyer-Villiger reaction with oxone; its demethylation with boron tribromide afforded nepetoidin B.