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Syntheses of gibberellins A93 and A94, natural products detected in wheat grain

Findlow, Stuart, Gaskin, Paul, Harrison, Polly A., Lenton, John R., Penny, Martin and Willis, Christine L. (1997) Syntheses of gibberellins A93 and A94, natural products detected in wheat grain Journal of the Chemical Society, Perkin Transactions 1, (5), pp. 751-758. (doi:10.1039/a604983d).

Record type: Article

Abstract

Extracts of mature wheat grain have been analysed by GC–MS and found to contain two new metabolites. The syntheses of the two new gibberellins, 1-hydroxy-2,3-epoxyGA9 4 and 1-hydroxy-2,3-epoxyGA20 5 from the fungal gibberellins, GA7 and GA3 are described. A range of protecting groups for the 7-carboxylic acid which can be removed under mild conditions, are compared. The allyl ester proved most valuable in the manipulation of these multifunctional molecules and it is removed with tetrakis(triphenylphosphine)palladium(0), triphenylphosphine and potassium isobutyrate. The structures of the new natural products in wheat were confirmed to be 4 and 5 by comparison with the GC–MS data from the synthetic samples and are assigned the trivial names GA94 and GA93 respectively.

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Published date: 1997

Identifiers

Local EPrints ID: 156665
URI: http://eprints.soton.ac.uk/id/eprint/156665
ISSN: 0300-922X
PURE UUID: 9ec51e1a-3705-41cd-87fa-28a007f3bbd2

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Date deposited: 01 Jun 2010 13:12
Last modified: 18 Jul 2017 12:42

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Contributors

Author: Stuart Findlow
Author: Paul Gaskin
Author: Polly A. Harrison
Author: John R. Lenton
Author: Martin Penny
Author: Christine L. Willis

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