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  • Title: Synthesis and bioactivity of the gibberellin, 18-hydroxy-GA1 (GA132).
    Author: Morrison E, Chandler PM, Thomson RJ, Mander LN.
    Journal: Org Biomol Chem; 2008 Apr 21; 6(8):1416-24. PubMed ID: 18385848.
    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 alpha-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 alpha-amylase induction assays.
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