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Steroids, XLVII: A facile synthesis of 3β-hydroxy-5α-cholest-8(14)-en-15-one
✍ Scribed by Tamás Bakos; Judit Horváth; Irén Vincze
- Publisher
- Elsevier Science
- Year
- 1992
- Tongue
- English
- Weight
- 303 KB
- Volume
- 63
- Category
- Article
- ISSN
- 0009-3084
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📜 SIMILAR VOLUMES
A four-step synthesis of 3 beta-hydroxy-5 alpha-cholest-8(14)-en-15-one (I) from 7-dehydrocholesterol is described. This synthesis, which is efficient and suitable for kilogram scale work, was carried out in a 33% overall average yield (39% overall best yield). A major byproduct of the hydrolysis of
## 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
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