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 language | English |
---|---|
Pages (from-to) | 4489-4493 |
Number of pages | 5 |
Journal | Tetrahedron Letters |
Volume | 45 |
Issue number | 23 |
DOIs | |
Publication status | Published - 31 May 2004 |
Externally published | Yes |
Keywords
- Bicyclo[2.2.2]diazaoctane
- Biosynthetic Diels-Alder reaction