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Total synthesis of the fumiquinazoline alkaloids: Solid-phase studies

Total synthesis of the fumiquinazoline alkaloids: Solid-phase studies
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.
1520-4766
186-194
Wang, H. S.
95a22b69-5405-4653-91d3-9bf3888c0b94
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9
Wang, H. S.
95a22b69-5405-4653-91d3-9bf3888c0b94
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9

Wang, H. S. and Ganesan, A. (1970) Total synthesis of the fumiquinazoline alkaloids: Solid-phase studies. Journal of Combinatorial Chemistry, 2 (2), 186-194. (doi:10.1021/cc9900807).

Record type: Article

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.

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Published date: 1 January 1970
Additional Information: <br />*ERROR Date not Compatible!! for field :date_issue Bad value :Mar Apr 2000*

Identifiers

Local EPrints ID: 18849
URI: http://eprints.soton.ac.uk/id/eprint/18849
ISSN: 1520-4766
PURE UUID: fd3859f7-b7dd-4398-bc83-2e22b29bc153

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Date deposited: 12 Dec 2005
Last modified: 22 Jul 2020 16:37

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Contributors

Author: H. S. Wang
Author: A. Ganesan

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