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Total synthesis of the fumiquinazoline alkaloids: Solution-phase studies

Total synthesis of the fumiquinazoline alkaloids: Solution-phase studies
Total synthesis of the fumiquinazoline alkaloids: Solution-phase studies
Biomimetic total syntheses of glyantrypine, fumiquinazoline F, fumiquinazoline G, and fiscalin B were achieved in four steps from tryptophan methyl ester. In the key step, the anthranilamide residue in a linear tripeptide is dehydrated to a benzoxazine by reaction with triphenylphosphine, iodine, and a tertiary amine. The benzoxazines subsequently undergo rearrangement to the natural products via an amidine intermediate. This dehydrative oxazine to quinazoline route is applicable to a broad range of N-acylanthranilamides, including sterically hindered cases.
quinazoline alkaloids, metabolites, 1, 4-benzodiazepine-2, 5-diones
0022-3263
1022-1030
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. (2000) Total synthesis of the fumiquinazoline alkaloids: Solution-phase studies. Journal of Organic Chemistry, 65 (4), 1022-1030. (doi:10.1021/jo9914364).

Record type: Article

Abstract

Biomimetic total syntheses of glyantrypine, fumiquinazoline F, fumiquinazoline G, and fiscalin B were achieved in four steps from tryptophan methyl ester. In the key step, the anthranilamide residue in a linear tripeptide is dehydrated to a benzoxazine by reaction with triphenylphosphine, iodine, and a tertiary amine. The benzoxazines subsequently undergo rearrangement to the natural products via an amidine intermediate. This dehydrative oxazine to quinazoline route is applicable to a broad range of N-acylanthranilamides, including sterically hindered cases.

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Published date: 25 February 2000
Keywords: quinazoline alkaloids, metabolites, 1, 4-benzodiazepine-2, 5-diones

Identifiers

Local EPrints ID: 18848
URI: http://eprints.soton.ac.uk/id/eprint/18848
ISSN: 0022-3263
PURE UUID: 79bc59ae-81f0-49c8-b070-089292cf27ad

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Date deposited: 12 Dec 2005
Last modified: 15 Mar 2024 06:08

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Contributors

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

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