Total synthesis of pederin

John C. Jewett, Viresh H. Rawal

Research output: Contribution to journalArticle

55 Scopus citations

Abstract

(Chemical Equation Presented) Blisteringly fast: The potent cytotoxic blistering agent pederin has been synthesized (see scheme). The synthesis is diastereoselective and concise (just 12 steps for the longest linear sequence), and features a formal hetero-Diels-Alder reaction of a hindered diene, a Mukaiyama-Michael reaction to set two additional stereocenters, and a Curtius rearrangement to stereospecifically introduce the aminal functionality.

Original languageEnglish (US)
Pages (from-to)6502-6504
Number of pages3
JournalAngewandte Chemie - International Edition
Volume46
Issue number34
DOIs
StatePublished - Sep 5 2007
Externally publishedYes

Keywords

  • Curtius rearrangement
  • Diastereoselectivity
  • Mukaiyama-Michael reaction
  • Natural products
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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