Please use this identifier to cite or link to this item: https://doi.org/10.1021/jo9914364
Title: Total synthesis of the fumiquinazoline alkaloids: Solution-phase studies
Authors: Wang, H. 
Ganesan, A. 
Issue Date: 25-Feb-2000
Citation: Wang, H., Ganesan, A. (2000-02-25). Total synthesis of the fumiquinazoline alkaloids: Solution-phase studies. Journal of Organic Chemistry 65 (4) : 1022-1030. ScholarBank@NUS Repository. https://doi.org/10.1021/jo9914364
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.
Source Title: Journal of Organic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/112141
ISSN: 00223263
DOI: 10.1021/jo9914364
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