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Liu, Shu-An; Trauner, Dirk (2017): Asymmetric Synthesis of the Antiviral Diterpene Wickerol A. In: Journal of the American Chemical Society, Vol. 139, No. 28: pp. 9491-9494
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Wickerol A (1) is an unusual diterpene with remarkable activity against the H1N1 influenza Virus. Its tetracyclic skeleton contains three quaternary carbons and is marked by several syn-pentane interactions which force a six-membered ring into a twist-boat conformation. We present an asymmetric synthesis of wickerol A (1) that is based on a Jung Diels-Alder reaction, an intramolecular alkylation to complete the 6-5-6-6 ring system, and a conjugate addition, all of which overcome considerable steric strain. During the synthesis, we isolated an unexpected cyclopropane that presumably stems from a carbonium ion intermediate.