A route to 24-epibrassinolide from ergosterol avoiding the use of osmium tetroxide

Abstract
A synthesis of (22R,23R)-2α,3α,22,23-tetrahydroxy-5α-ergostan-6-one (V) from the dienone IV via the diepoxide XXII is described. The tetrol V is a key intermediate in the synthesis of 24-epibrassinolide. The reactivity of the side chain was studied on 5α-ergost-22-en-6-one (XIV) as a model compound. 1H and 13C NMR spectra of 24-epibrassinolide derivatives are discussed.

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