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 and structure of 15-oxygenated 5α,14β-cholest-7-en-3β-ol derivatives
✍ Scribed by E.J. Parish; M.E. Newcomer; G.L. Gilliland; F.A. Quiocho; G.J. Schroepfer Jr.
- Book ID
- 118367410
- Publisher
- Elsevier Science
- Year
- 1976
- Tongue
- French
- Weight
- 225 KB
- Volume
- 17
- Category
- Article
- ISSN
- 0040-4039
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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
The chemical synthesis of 3beta-bromobenzoyloxy-14alpha, 15alpha-epoxy-5alpha-cholest-7-ene is described. Single crystal structral analysis was employed to unambiguously determine the location and absolute configuration of the epoxide moiety in the 3beta-p-bromobenzoyloxy-14alpha, 15alpha-epoxy-5alp
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