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

Syntheses of gibberellins A93 and A94, natural products detected in wheat grain
Syntheses of gibberellins A93 and A94, natural products detected in wheat grain
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.
0300-922X
751-758
Findlow, Stuart
59a414f6-5249-4265-bedf-d36a40bdf4e8
Gaskin, Paul
d179b81b-58be-4ad9-b7be-bd6cd5242f26
Harrison, Polly A.
db6daefe-4e46-4db8-b334-58fb84b77469
Lenton, John R.
90bb9087-83c0-4b47-86e7-b8068b91fe2a
Penny, Martin
bd3b8f99-01d4-4bda-951c-72ebd7724390
Willis, Christine L.
6881fcba-a445-48db-a8b6-fc21331cb90b
Findlow, Stuart
59a414f6-5249-4265-bedf-d36a40bdf4e8
Gaskin, Paul
d179b81b-58be-4ad9-b7be-bd6cd5242f26
Harrison, Polly A.
db6daefe-4e46-4db8-b334-58fb84b77469
Lenton, John R.
90bb9087-83c0-4b47-86e7-b8068b91fe2a
Penny, Martin
bd3b8f99-01d4-4bda-951c-72ebd7724390
Willis, Christine L.
6881fcba-a445-48db-a8b6-fc21331cb90b

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), 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: https://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: 19 Jul 2019 23:19

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