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Total Synthesis of the Fumiquinazoline Alkaloids: Solid-Phase Studies

2000; American Chemical Society; Volume: 2; Issue: 2 Linguagem: Inglês

10.1021/cc9900807

1520-4774

Haishan Wang, A. Ganesan,

Synthetic Organic Chemistry Methods

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.