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

✍ Scribed by Edward J. Parish; Mitsuhiro Tsuda; George J. Schroepfer Jr.

Publisher
Elsevier Science
Year
1979
Tongue
English
Weight
875 KB
Volume
24
Category
Article
ISSN
0009-3084

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✦ Synopsis

Treatment of 3~-benzoyloxy-14c¢,l 5~-epoxy-5a-cholest-7-ene (I) with gaseous HCI in chloroform at 40°C gave, in 87% yield, 3#-benzoyloxy-7a,1513-dichloro-5a-cholest-8(14)-ene (111). Reduction of the latter compound with lithium aluminum hydride in ether at room temperature for 20 min gave, in 86% yield, 7~-15/3-dichloro-Sa-cholest-8( 14)-en-3~-ol (IV). The latter compound was fully characterized and assignments of the individual carbon peaks in the 13 C 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, 5a-eholesta-7,14-dien-3~-ol (VI). Reduction of the dichloro-steryl benzoate Ili with lithium triethylborohydride in tetrahydrofuran gave, in 88% yield, 5~-cholest-8( 14)-en-3~3-ol (VII). A similar reduction using lithium triethylborodeuteride led to the formation of [ 7~3,15/~ -2 H 2 ]-Vlla. Treatment of III with concentrated HCI in a mixture of chloroform and methano' gave, in 79% yield, 3t3-benzoyloxy-5~-cholest-8(14)-en-15-one (II) which was characterized as such and as the corresponding free sterol.

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