Synthesis of Oxorhenium(V) Complexes Derived from 7α-Functionalized Testosterone: First Rhenium-Containing Testosterone Derivatives

✍ Scribed by Frank Wüst; Dieter Scheller; Hartmut Spies; Bernd Johannsen

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 404 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-1948
• DOI: 10.1002/(sici)1099-0682(199806)1998:6<789::aid-ejic789>3.0.co;2-z

✦ Synopsis

In an effort to assist in the preparation of metal-containing ligands for the androgen receptor, we have synthesized the first oxorhenium(V) complexes containing a pendant testosterone moiety. The key step in the synthesis involves the copper-catalysed, α-selective 1,6-Michael addition of a 4pentenylmagnesium bromide to 6-dehydrotestosterone 17βacetate. The α-stereoselectivity is governed by the presence of the C-19 methyl group. The absolute configurations of the