Total synthesis of the fumiquinazoline alkaloids: solid-phase studies.
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.
Wang
H
H
Institute of Molecular and Cell Biology, National University of Singapore.
Ganesan
A
A
D000470:Alkaloids / Q000138:chemical synthesis*; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D009842:Oligopeptides / Q000138:chemical synthesis; D019151:Peptide Library; D011799:Quinazolines / Q000138:chemical synthesis*; D062367:ortho-Aminobenzoates / Q000138:chemical synthesis
D000470:Alkaloids; D009842:Oligopeptides; D019151:Peptide Library; D011799:Quinazolines; D062367:ortho-Aminobenzoates