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Sterol synthesis. Chemical synthesis of 3β-benzoyloxy -14α, 15α-epoxy-5α-cholest-7-ene, a key intermediate in the synthesis of 15-oxygenated sterols

✍ Scribed by Edward J. Parish; Thomas E. Spike; George J. Schroepfer Jr.


Book ID
107736888
Publisher
Elsevier Science
Year
1977
Tongue
English
Weight
389 KB
Volume
18
Category
Article
ISSN
0009-3084

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📜 SIMILAR VOLUMES


Sterol synthesis. Synthesis of 15-oxygen
✍ 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~,

Crystal structure of 3β-benzoyloxy-6α-ch
✍ David K. Wilson; William K. Wilson; Florante A. Quiocho; George J. Schroepfer Jr 📂 Article 📅 1988 🏛 Elsevier Science 🌐 English ⚖ 441 KB

The X-ray crystal structure of 3~-benzoyloxy-6a-chloro-5a-cholest-7-ene (IV) was determined by the heavy atom method and ref'med to R ---0.063 (space group P2s, a --11.364, b = 11.089, c --12.232,/~ = 99.43 °, Z ---2). IV was previously shown to be an important intermediate in the acid-catalyzed iso

Synthesis, properties and reactions of 3
✍ 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