Steroid Series. XVII. New Synthetic Routes to 19-Norsteroids (1)
- 1 January 1967
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 15 (1) , 27-37
- https://doi.org/10.1248/cpb.15.27
Abstract
19-Nor- [DELTA]4-3-oxosteroid was synthesized starting from 3[alpha],5[alpha]-cyclo-6[beta],19-oxidosteroid through 3[beta]-substituted- 5-steroid-19-oic acid, whose synthesis was achieved by 3 methods: Hydrolysis of [beta]-hydroxy- A5-steroid-19-oic acid 3,19-lactone which was prepared by oxidizing either 3[beta],19-dihydroxy- [DELTA]5-steroid or 3[beta]-hydroxy-19-oxo-[DELTA]5-steroid with Jones reagent or Oppenauer reaction, oxidation of 3[beta],19-dihydroxy- [DELTA]5-steroid 3-acetate with the excess Jones reagent, or reduction of 3[alpha],5[alpha]-cyclo-6-oxo-19-oic acid with sodium borohydride and subsequent acid-catalysed solvolysis of a mixture of resultant 6-epimeric hydroxy acids in a suitable solvent. 3[beta]Substituted- [DELTA]5-steroid-19-oic acid was in turn converted to 19-nor-[DELTA]4-3-oxosteroid in 2 ways: Oxidation of 3[beta]-hydroxy compound and subsequent acid-treatment of the resultant [DELTA]5-3-oxosteroid-19-oic acid, or pyrolysis of the 3[beta]-acetoxy- [DELTA]5-steroid-19-oic acid to afford 3[beta]-acetoxy- [DELTA]5(10)-steroid, followed by alkaline hydrolysis, Jones oxidation, and acid-treatment, successively.This publication has 0 references indexed in Scilit: