1029302-49-5Relevant academic research and scientific papers
Synthesis and bioactivity of the gibberellin, 18-hydroxy-GA1 (GA132)
Morrison, Ellen,Chandler, Peter M.,Thomson, Regan J.,Mander, Lewis N.
, p. 1416 - 1424 (2008)
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-GA 4 relative, have been confirmed in dwarf barley growth and α-amylase induction assays. The Royal Society of Chemistry.
