Synthesis, stability and biological activity of 19-desoxy-gibberellins A1 and A3
1993
Ward, J.L. | Reynolds, G.J. | Hooley, R. | Beale, M.H.
The synthetic conversion of gibberellin A3 (GA3) to the 19-desoxy-derivatives of GA1 and GA3 is described. The key steps involve regiospecific reduction of the known GA3 hydrogenolysis product at the C-19 carboxyl group via treatment of the acyl chloride with zinc borohydride, followed by an iodocyclization of the resultant alcohol. 19-Desoxy-GA1 and GA3 are stable in alkali, unlike their parent lactones GA1 and GA3. Both derivatives are biologically active in inducing alpha-amylase production in protoplasts of Avena fatua aleurone. They have biological activities of one order of magnitude less than that of the natural analogues. These data reveal the significant contribution of the lactone carbonyl to the observed response (receptor affinity) of GA1 and GA3.
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