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), 1022-1030. (doi: 10.1021/jo9914364).

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Description/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.

Item Type: Article
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Keywords: quinazoline alkaloids, metabolites, 1,4-benzodiazepine-2,5-diones
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 18848
Date Deposited: 12 Dec 2005
Last Modified: 27 Mar 2014 18:08
URI: http://eprints.soton.ac.uk/id/eprint/18848

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