Synthesis, properties and reactions of 3β-benzoyloxy-7α-15β-dichloro-5α-cholest-8(14)-ene

Add time:09/02/2019    Source:sciencedirect.com

Treatment of 3β-benzoyloxy-14α,15α-epoxy-5α-cholest-7-ene (I) with gaseous HCl in chloroform at −40°C gave, in 87% yield, 3β-benzoyloxy-7α,15β-dichloro-5α-cholest-8(14)-ene (III). Reduction of the latter compound with lithium aluminum hydride in ether at room temperature for 20 min gave, in 86% yield, 7α-15β-dichloro-5α-cholest-8(14)-en-3β-ol (IV). The latter compound was fully characterized and assignments of the individual carbon peaks in the 13C nuclear magnetic resonance spectra of this sterol have been completed. Reduction of III with excess lithium aluminum hydride in refluxing ether for 4 days gave, in 74% yield, 5α-cholesta-7,14-dien-3β-ol (VI). Reduction of the dichloro-steryl benzoate III with lithium triethylborohydride in tetrahydrofuran gave, in 88% yield, 5α-cholest-8(14)-en-3β-ol (VII). A similar reduction using lithium triethylborodeuteride led to the formation of [7β,15ξ-2H2]-VIIa. Treatment of III with concentrated HCl in a mixture of chloroform and methanol gave, in 79% yield, 3β-benzoyloxy-5α-cholest-8(14)-en-15-one (II) which was characterized as such and as the corresponding free sterol.

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