Syntheses and structural confirmations of members of a heterocycle- containing family of labdane diterpenoids

Daniel J. MacK, Jon T. Njardarson

Research output: Contribution to journalArticle

18 Scopus citations

Abstract

Building with berries! Several labdane natural products have been synthesized for the first time by the combination of a copper-catalyzed vinyl oxirane ring expansion reaction with an abundant, inexpensive, chiral natural source (juniper berries; see scheme). These expedient (1-5 step) syntheses have resulted in the structural confirmations of five natural products and one reassignment. Reagent-controlled oxidation and 1,3-diene isomerization results are also presented.

Original languageEnglish (US)
Pages (from-to)1543-1547
Number of pages5
JournalAngewandte Chemie - International Edition
Volume52
Issue number5
DOIs
StatePublished - Jan 28 2013

Keywords

  • labdanes
  • olefin isomerization
  • ring expansion
  • total synthesis
  • vinyl oxiranes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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