Total synthesis of vinigrol

Qingliang Yang, Jon T. Njardarson, Cristian Draghici, Fang Li

Research output: Contribution to journalArticle

50 Scopus citations

Abstract

Carbocyclic cage fight: The substrate-controlled total synthesis of vinigrol features a strategic oxidative dearomatization/Diels-Alder cycloaddition reaction and a subsequent palladium-catalyzed cyclization cascade to construct the carbocyclic core. The C4, C9, and C12 stereocenters were installed using either reduction or oxidation reactions, and the diterpenoid core was unraveled by a ring fragmentation reaction.

Original languageEnglish (US)
Pages (from-to)8648-8651
Number of pages4
JournalAngewandte Chemie - International Edition
Volume52
Issue number33
DOIs
StatePublished - Aug 12 2013

Keywords

  • dearomatization
  • hydrogenation
  • natural products
  • terpenoids
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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