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7α,15β-Dichloro-5α-cholest-8(14)-en-3β-ol, a novel inhibitor of sterol biosynthesis in animal cells

✍ Scribed by George J. Schroepfer Jr.; Edward J. Parish; Gary L. Gilliland; Marcia E. Newcomer; Laura L. Sommerville; Florante A. Quiocho; Andrew A. Kandutsch

Book ID
118312512
Publisher
Elsevier Science
Year
1978
Tongue
English
Weight
409 KB
Volume
84
Category
Article
ISSN
0006-291X

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Sterol synthesis. Synthesis of 15-oxygen
Sterol synthesis. Synthesis of 15-oxygenated 5α, 14β-cholest-7-en-3β-ol derivatives
✍ Edward J. Parish; George J. Schroepfer Jr. 📂 Article 📅 1977 🏛 Elsevier Science 🌐 English ⚖ 918 KB

Treatment of 3~.benzoyloxy-140, 15wepoxy-5(~.cholesg-7-ene with boron trifluoride-etherate 8ave, in 43% yield, 30-benzoyloxy-Sa, 14~cholest-7-en,15-one with the unnatt~ral C-D ring juncture, Reduction of the latteg compound with lithium aluminum hydride gave 15a, 14O-~holest-7.en'3p, 15wdiol and 5~,

Synthesis, properties and reactions of 3
Synthesis, properties and reactions of 3β-benzoyloxy-7α-15β-dichloro-5α-cholest-8(14)-ene
✍ Edward J. Parish; Mitsuhiro Tsuda; George J. Schroepfer Jr. 📂 Article 📅 1979 🏛 Elsevier Science 🌐 English ⚖ 875 KB

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% yi