The Realization of an Oxidative Dearomatization-Intramolecular Diels-Alder Route to Vinigrol

Cristian Draghici, Jon T Njardarson

Research output: Contribution to journalArticle

Abstract

Detailed in this chapter is the Njardarson group vinigrol total synthesis saga. Even though the Njardarson group synthetic strategy had undergone multiple modifications over time, it remained faithful to several key reaction design elements, namely: (a) oxidative dearomatization/Diels-Alder cascade, (b) radical or palladium cascade, (c) creation of a tetracyclic cage for substrate control purposes, and (d) a late-stage C-C bond fragmentation reaction to unravel the vinigrol core. The saga begins with the earliest oxidative dearomatization explorations followed by detailed descriptions of the modifications that were made in response to the obstacles encountered en route to the completed total synthesis of vinigrol.

Original languageEnglish (US)
Pages (from-to)335-376
Number of pages42
JournalStrategies and Tactics in Organic Synthesis
Volume11
DOIs
Publication statusPublished - 2015

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Keywords

  • Adler-Becker oxidation
  • Allylic oxidation
  • Diels-Alder
  • Fragmentation
  • Hypervalent iodide
  • Lead(IV) acetate
  • Oxidative dearomatization
  • Palladium cyclization
  • Radical cyclization
  • Samarium diiodide
  • Selenium dioxide
  • Trifluoroethyl ether
  • Vinigrol
  • Wessely oxidation

ASJC Scopus subject areas

  • Organic Chemistry
  • Drug Discovery

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