Issue 13, 1976

Synthesis of isomeric 5α-androstane-3,15,17β-triols

Abstract

3α-Acetoxy-16α-bromo-5α-androstan-17-one (1) was converted into 16α-bromo-17,17-ethylenedioxy-5α-androstan-3α-ol (2), which was dehydrobrominated and hydrolysed to give 3α-hydroxy-5α-androst-15-en-17-one (5). Addition of benzyl alcohol to the Δ15-3α-ol (5) followed by hydrogenolysis yielded 3α, 15β-dihydroxy-5α-androstan-17-one (7). This was converted into 5α-androstane-3α, 15β, 17β-triol (8). Similarly 5α-androstane-3β, 15β, 17β-triol (10) was prepared from 3β-hydroxy-5α-androst-15-en-17-one (3). Hydroboration of 5α-androst-14-ene-3α, 17β-diol (12) afforded 5α-androstane-3α, 15α-17β-triol (13). The spectral properties of 5α-androstane-3,15,17β-triols are markedly affected by the configuration of the hydroxy-group at C-15.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1976, 1429-1432

Synthesis of isomeric 5α-androstane-3,15,17β-triols

M. Matsui and Y. Kinuyama, J. Chem. Soc., Perkin Trans. 1, 1976, 1429 DOI: 10.1039/P19760001429

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements