Total synthesis of the tremorgenic indole diterpene paspalinine

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38 Citations (Scopus)

Abstract

Succinct and stereoselective: A high-yielding two-step indole ring installation comprising the Stille cross-coupling and a PdII-mediated oxidative heterocyclization was exploited in a concise total synthesis of paspalinine. The trans-anti-trans CDE fused ring system of the heptacyclic natural product was established highly stereoselectively through hydroxy-directed cyclopropanation and allylic selenoxide rearrangement.

Original languageEnglish
Pages (from-to)12833-12836
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number51
DOIs
Publication statusPublished - 2012 Dec 14

Keywords

  • alkaloids
  • natural products
  • palladium
  • paspalinine
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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