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Total synthesis of the fumiquinazoline alkaloids: Solution-phase studies

Wang, H. S. and Ganesan, A. (2000) Total synthesis of the fumiquinazoline alkaloids: Solution-phase studies Journal of Organic Chemistry, 65, (4), pp. 1022-1030. (doi:10.1021/jo9914364).

Record type: Article


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


Local EPrints ID: 18848
ISSN: 0022-3263
PURE UUID: 79bc59ae-81f0-49c8-b070-089292cf27ad

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Date deposited: 12 Dec 2005
Last modified: 17 Jul 2017 16:34

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

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