Asymmetric Synthesis of the Antiviral Diterpene Wickerol A

Liu, Shu-An und Trauner, Dirk (2017): Asymmetric Synthesis of the Antiviral Diterpene Wickerol A. In: Journal of the American Chemical Society, Bd. 139, Nr. 28: S. 9491-9494

Abstract

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.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0002-7863
• Sprache: Englisch