A Diels-Alder macrocyclization enables an efficient asymmetric synthesis of the antibacterial natural product abyssomicin C

Christoph W. Zapf, Bryce A. Harrison, Carmen Drahl, Erik J. Sorensen

Research output: Contribution to journalArticle

74 Scopus citations

Abstract

An efficient and highly diastereoselective intramolecular Diels-Alder reaction is the basis of a concise asymmetric synthesis of the potent antibacterial natural product abyssomicin C (see formula). The complexity of the target structure was reduced to three fragments and required two carbonyl addition reactions to achieve key bond formations. (Figure Presented).

Original languageEnglish (US)
Pages (from-to)6533-6537
Number of pages5
JournalAngewandte Chemie - International Edition
Volume44
Issue number40
DOIs
StatePublished - Oct 14 2005

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • Desymmetrization
  • Diels-Alder reaction
  • Enzymes
  • Natural products

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