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Studies towards the synthesis of diazonamide A. Unexpected formation of a 3,4-bridged indole

Moody, Christopher J., Doyle, Kevin J., Elliott, Mark Christopher and Mowlem, Timothy J. 1997. Studies towards the synthesis of diazonamide A. Unexpected formation of a 3,4-bridged indole. Journal of the Chemical Society, Perkin Transactions 1 1997 (16) , pp. 2413-2420. 10.1039/a700684e

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Abstract

Model studies towards the synthesis of the cytotoxic marine natural product diazonamide A are described. Three model 3-phenylbenzo[b]furan derivatives 5, 8 and 10 were prepared using rhodium(II) catalysed decomposition of the diazophenylacetate 3, Claisen rearrangement of the ether 7, and a classical intramolecular Friedel–Crafts reaction as key steps. Only the aromatic benzofuran system proved satisfactory in palladium coupling reactions; diazoacetyl(benzofuranyl)indole 18 was prepared by Suzuki coupling of (benzofuran-7-yl)boronic acid 11 with 4-bromoindole 14 to give 17, followed by diazo-transfer. Rhodium(II) catalysed decomposition of 18 in acetonitrile resulted in the formation of the 3,4-bridged indole 19 rather than the desired oxazole 20.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: RSC Publishing
ISSN: 0300-922X
Last Modified: 04 Jun 2017 04:29
URI: http://orca.cf.ac.uk/id/eprint/39951

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