Novel gibberellin ring a epoxy alcohols: synthesis and X-ray molecular structure

Abstract

The syntheses of four new gibberellin vicinal epoxy alcohols are described. The 1α-hydroxy 2β,3β-epoxides 3 and 9 were prepared in good yield from the corresponding ring A iodo diol 2 or 8via dehydrohalogenation followed by a Payne-type rearrangement. The structure of compound 3 was confirmed by X-ray crystallography. Although the 2β,3β-epoxide GA₆11 is a natural product, neither of the 1α-hydroxy derivatives was found to be naturally occurring.