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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| 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 |
| Item ID: | 18848 |
| Date Deposited: | 12 Dec 2005 |
| Last Modified: | 01 Jun 2011 06:11 |
| Contributors: | Wang, H. S. (Author) Ganesan, A. (Author) |
| Date: | 25 February 2000 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/18848 |
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