The University of Southampton
University of Southampton Institutional Repository

Total synthesis of the fumiquinazoline alkaloids: Solution-phase studies

Record type: Article

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.

Full text not available from this repository.

Citation

Wang, H. S. and Ganesan, A. (2000) Total synthesis of the fumiquinazoline alkaloids: Solution-phase studies Journal of Organic Chemistry, 65, (4), pp. 1022-1030. (doi:10.1021/jo9914364).

More information

Published date: 25 February 2000
Keywords: quinazoline alkaloids, metabolites, 1, 4-benzodiazepine-2, 5-diones

Identifiers

Local EPrints ID: 18848
URI: http://eprints.soton.ac.uk/id/eprint/18848
ISSN: 0022-3263
PURE UUID: 79bc59ae-81f0-49c8-b070-089292cf27ad

Catalogue record

Date deposited: 12 Dec 2005
Last modified: 17 Jul 2017 16:34

Export record

Altmetrics

Contributors

Author: H. S. Wang
Author: A. Ganesan

University divisions


Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×