3α-Hydroxycholest-9(11)-ene was converted into 9α,11αa-epoxycholesta-1,4-diene-3-one (12), which, on treatment with lithium aluminium hydride, underwent dienol-benzene cleavage of the 9,10-bond, giving the epimeric 9-hydroxy-9,10-seco-1,3,5(10)-cholestatrienes (14) and (15). These were further degraded to 8α-hydroxymethyl-des-AB-cholestane (19).
B. Lythgoe and D. A. Roberts, J. Chem. Soc., Perkin Trans. 1, 1980, 892 DOI: 10.1039/P19800000892
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