## Abstract Oxidation of 5α‐cholest‐8(14)‐ene‐3β,7α,15α‐triol with silver carbonate‐celite gave 5α‐cholest‐8(14)‐ene‐7α,15α‐diol‐3‐one in 88% yield. Treatment of the latter compound with tritiated water under basic conditions gave a labeled product which was reduced with lithium tri‐__tert__‐butoxy
Sterol synthesis. Synthesis of 15-oxygenated 5α, 14β-cholest-7-en-3β-ol derivatives
✍ Scribed by Edward J. Parish; George J. Schroepfer Jr.
- Publisher
- Elsevier Science
- Year
- 1977
- Tongue
- English
- Weight
- 918 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0009-3084
No coin nor oath required. For personal study only.
✦ Synopsis
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~, 14pcholest-7-en-3#, 15~-cliol in 9% and 81% yields, ~espectively.
📜 SIMILAR VOLUMES
The chemical synthesis of 3 beta-p-bromobenzoyloxy-15 beta-methyl-5 alpha,14 beta-cholest-7-en-15 alpha-ol from 15 beta-methyl-5 alpha, 14 beta-cholest-7-ene-3 beta,15 alpha-diol is described. The structure of the former compound was unambiguously determined by X-ray crystallographic analysis. The s
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
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