An efficient substrate-controlled approach towards hypoestoxide, a member of a family of diterpenoid natural products with an inside-out [9.3.1]bicyclic core

Nicholas A. McGrath, Christopher A. Lee, Hiroshi Araki, Matthew Brichacek, Jon T. Njardarson

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

(Chemical Equation Presented) The bicycle works: A versatile route to the verticillane family of natural products has been devised, utilizing a strategically rigidified relay ring-closing metathesis reaction. The shape of the bicyclic product was used to stereoselectively control the bisepoxidation reaction towards hypoestoxide, a member of this natural product family.

Original languageEnglish (US)
Pages (from-to)9450-9453
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number49
DOIs
StatePublished - Nov 24 2008
Externally publishedYes

Keywords

  • Atropisomerism
  • Cyclization
  • Hypoestoxide
  • Natural products
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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