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A 15-hydroxy group prevents the steviol/isosteviol rearrangement taking place. In the presence of hydrobromic acid, the 15α-alcohol undergoes rearrangement to a 17-alcohol whilst the 15β-alcohol gives the 15-ketones. Treatment of a 15α-hydroxy-16,17-epoxide gives the 15α,16α-dihydroxy-17-bromide, the structure of which was confirmed by X-ray analysis.
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Avent et al. (1990) studied this question.
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