Gold(I) as an artificial cyclase: Short stereodivergent syntheses of (-)-epiglobulol and (-)-4β,7α- and (-)-4α,7α- aromadendranediols

Javier Carreras, Madeleine Livendahl, Paul R. McGonigal, Antonio M. Echavarren

Research output: Contribution to journalArticlepeer-review

Abstract

Three natural aromadendrane sesquiterpenes, (-)-epiglobulol, (-)-4β,7α-aromadendranediol, and (-)-4α,7α- aromadendranediol, have been synthesized in only seven steps in 12, 15, and 17% overall yields, respectively, from (E,E)-farnesol by a stereodivergent gold(I)-catalyzed cascade reaction which forms the tricyclic aromadendrane core in a single step. These are the shortest total syntheses of these natural compounds.

Original languageEnglish
Pages (from-to)4896-4899
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number19
DOIs
Publication statusPublished - 5 May 2014

Keywords

  • cyclization
  • gold
  • natural products
  • terpenoids
  • total synthesis

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