Concise synthesis of the core bicyclo[2.2.2]diazaoctane ring common to asperparaline, paraherquamide, and stephacidin alkaloids

Luke A. Adams, Chandele R. Gray, Robert M. Williams

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26 Citations (Scopus)

Abstract

A versatile synthesis of the bicyclo[2.2.2]diazaoctane core structure of asperparaline, brevianamide, paraherquamide, and stephacidin natural products is demonstrated. This convergent synthesis relies on an intramolecular hetero Diels-Alder reaction to construct the key tetracycle from a diketopiperazine derived azadiene; which in turn was formed from prolinamide and a pyruvic acid derivative. The stereochemical outcome of the Diels-Alder reaction was found to favor the brevianamide stereochemistry.

Original languageEnglish
Pages (from-to)4489-4493
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number23
DOIs
Publication statusPublished - 31 May 2004
Externally publishedYes

Keywords

  • Bicyclo[2.2.2]diazaoctane
  • Biosynthetic Diels-Alder reaction

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