Asymmetric Synthesis of the Antiviral Diterpene Wickerol A

Shu An Liu, Dirk Trauner

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)9491-9494
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number28
DOIs
StatePublished - Jul 19 2017

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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