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A stereoselective synthesis of the side-chain of brassinolide which involves β-alkylative 1,3-carbonyl transposition of the α,β-unsaturated ketone 3,6-diacetoxycholest-22-en-24-one is described. The overall yield of (22R,23R,24S)-22,23-isopropylidenedioxy-24-methyl-5β-cholestane-3α,6α-diol from 3α,6α-diacetoxy-5β-pregnane-20-carbaldehyde in six steps is 47%.
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Shen et al. (1990) studied this question.
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