Total synthesis of the fumiquinazoline alkaloids: solid-phase studies.

Abstract

We have previously described an efficient four-step synthesis of the fumiquinazoline alkaloids (Wang, H.; Ganesan, A. J. Org. Chem. 1998, 63, 2432-2433). Here, we demonstrate that this route is readily adaptable to combinatorial synthesis on solid phase. Linear tripeptides containing a central anthranilate unit were assembled on the Wang resin and subjected to dehydration and cyclative release to yield the pyrazino[2,1-b]quinazoline-3,6-diones in high purity. To demonstrate the scope of this protocol, a small library [ca. 20 compounds] of unnatural analogues was prepared by parallel synthesis.

• Authors: H Wang, A Ganesan
• Journal: Journal of combinatorial chemistry (J Comb Chem) 2000 Mar-Apr Vol. 2 Issue 2 Pg. 186-94 ISSN: 1520-4766 [Print] United States
• PMID: 10757098 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Alkaloids
• Oligopeptides
• Peptide Library
• Quinazolines
• ortho-Aminobenzoates

Topics

• Alkaloids (chemical synthesis)
• Cyclization
• Magnetic Resonance Spectroscopy
• Oligopeptides (chemical synthesis)
• Peptide Library
• Quinazolines (chemical synthesis)
• ortho-Aminobenzoates (chemical synthesis)