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.
|Keywords:||quinazoline alkaloids, metabolites, 1,4-benzodiazepine-2,5-diones|
Q Science > QD Chemistry
|Divisions:||University Structure - Pre August 2011 > School of Chemistry
|Date Deposited:||12 Dec 2005|
|Last Modified:||27 Mar 2014 18:08|
|RDF:||RDF+N-Triples, RDF+N3, RDF+XML, Browse.|
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