Syntheses of gibberellins A93 and A94, natural products detected in wheat grain
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,
1β-hydroxy-2β,3β-epoxyGA9 4 and
1β-hydroxy-2β,3β-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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