1. Asymmetric Synthesis of the Antiviral Diterpene Wickerol A.
- Author
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Liu, Shu-An and Trauner, Dirk
- Subjects
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DITERPENES , *TERPENES , *INFLUENZA A virus, H1N1 subtype , *DIELS-Alder reaction , *CHEMICAL reactions - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2017
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