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Issue 8, 2008
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Synthesis and bioactivity of the gibberellin, 18-hydroxy-GA1 (GA132)

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Abstract

As part of a study to confirm putative structural assignments to new gibberellins and to furnish sufficient quantities for biological investigations, a twenty step synthesis of 18-hydroxy GA1 from gibberellic acid (GA3) is described, allowing the confirmation of structure for a new gibberellin, GA132, that occurs in developing grains of barley (Hordeum vulgare). The early part of the sequence involved cleavage of the C(3)–C(4) bond in the A-ring of a 3-oxo intermediate. The ring was then reformed as part of a “domino” process involving the conjugate addition of alkoxide to an α-methylene lactone moiety followed by an intramolecular aldol reaction. The bioactivities of the new GA, and its 18-hydroxy-GA4 relative, have been confirmed in dwarf barley growth and α-amylase induction assays.

Graphical abstract: Synthesis and bioactivity of the gibberellin, 18-hydroxy-GA1 (GA132)

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Publication details

The article was received on 15 Jan 2008, accepted on 01 Feb 2008 and first published on 26 Feb 2008


Article type: Paper
DOI: 10.1039/B800728D
Citation: Org. Biomol. Chem., 2008,6, 1416-1424
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    Synthesis and bioactivity of the gibberellin, 18-hydroxy-GA1 (GA132)

    E. Morrison, P. M. Chandler, R. J. Thomson and L. N. Mander, Org. Biomol. Chem., 2008, 6, 1416
    DOI: 10.1039/B800728D

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