Location: Dairy Forage ResearchTitle: Synthesis of nepetoidin B
|TIMOKHIN, VITALIY - University Of Wisconsin|
|REGNER, MATTHEW - University Of Wisconsin|
|TSUJI, YUKIKO - University Of Wisconsin|
|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.