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).

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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