Steroid Series. XVI. The Preparation of 3α, 5α-Cyclo-6β, 19-oxidosteroids and its Conversion to 19-Oxygenated Steroid Derivatives
- 1 January 1967
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 15 (1) , 15-27
- https://doi.org/10.1248/cpb.15.15
Abstract
3α, 5α-Cyclo-6β, 19-oxidosteroid (II) was synthesized by the lead tetraacetate oxidation of 3α, 5α-cyclo-6β-hydroxysteroid (I) in benzene. The acid-catalysed solvolysis of the oxide (II) afforded 3α, 5α-cyclo-19-hydroxy-6β-substituted steroid (XVI) and/or Δ5-19-hydroxy-3β-substituted steroid (XVII), depending upon the reaction conditions employed. Oxidation of the oxide (II) with Jones reagent gave 3α, 5α-cyclo-6β, 19-dioxosteroid (XIX) with two equivalent molar oxidant, and 3α, 5α-cyclo-6-oxosteroid-19-oic acid (XX) with the excess reagent.This publication has 2 references indexed in Scilit:
- Reaktionen von Steroid‐Hypojoditen IV. Über den Verlauf intramolekularer Substitutionsreaktionen, insbesondere bei 2β‐ und 4β‐Hydroxysteroiden. Über Steroide, 192. MitteilungHelvetica Chimica Acta, 1961
- Über Steroide und Sexualhormone. 223. Mitteilung. UV.‐Bestrahlung von 11‐Oxo‐Steroiden I Die Darstellung von 11β, 19‐Cyclo‐, 9β, 19‐Cyclo‐ und 19‐Hydroxy‐5α‐pregnan‐VerbindungenHelvetica Chimica Acta, 1961