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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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
Digital Object Identifier (DOI): doi:10.1021/jo9914364
Related URLs:
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
Accepted Date and Publication Date:
25 February 2000Published
Date Deposited: 12 Dec 2005
Last Modified: 31 Mar 2016 11:35

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