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Synthesis of Oxorhenium(V) Complexes Derived from 7α‐Functionalized Testosterone: First Rhenium‐Containing Testosterone Derivatives
Author(s) -
Wüst Frank,
Scheller Dieter,
Spies Hartmut,
Johannsen Bernd
Publication year - 1998
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(199806)1998:6<789::aid-ejic789>3.0.co;2-z
Subject(s) - chemistry , rhenium , ligand (biochemistry) , moiety , bromide , epimer , stereochemistry , metal , androgen receptor , stereoselectivity , medicinal chemistry , combinatorial chemistry , organic chemistry , receptor , catalysis , medicine , biochemistry , prostate cancer , cancer
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 4‐pentenylmagnesium bromide to 6‐dehydrotestosterone 17β‐acetate. The α‐stereoselectivity is governed by the presence of the C‐19 methyl group. The absolute configurations of the epimers were investigated by 1 H‐NMR studies. Further chemical transformations of the 7α‐pentenyl spacer introduced the terminal thiol group, needed for complex formation. The complex formation was accomplished by the “3+1” mixed‐ligand concept using two different rhenium precursors. The obtained complexes differ with respect to the central donor atom of the tridentate ligand part, namely, S and O.