Whereas gibberellin A3 is completely rearranged by 0.01 M-aqueous sodium hydroxide at 22 °C to the 19,2-lactone, the methyl ethers of both reactant and product, the 3-epimer (as its 13-acetate), and 3-deoxygibberellin A3 methyl ester are all inert to aqueous base. A 2β,3β-epoxy-19-carboxylate intermediate in the rearrangement is proposed.
P. S. Kirkwood, J. MacMillan and M. L. Sinnott, J. Chem. Soc., Perkin Trans. 1, 1980, 2117 DOI: 10.1039/P19800002117
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