Synthesis and chemical reactions of the steroidal hormone 17α-methyltestosterone

• Chemical and microbial methods of synthesis of 17α-methyltestosterone.
• Radical deoxygenation and irradiation of the testosterone skeleton.
• Steroidal O-glucuronidation, O-silylation and heterocyclic synthesis are presented.
• Biotransformation of 17α-methyltestosterone.
• Medicinal importance of 17α-methyltestosterone.

Structural modifications of natural products with complex structures like steroids require great synthetic effort. A review of literature is presented on the chemistry of the steroidal hormone 17α-methyltestosterone that is approved by Food and Drug Administration (FDA) in the United States as an androgen for estrogen–androgen hormone replacement therapy treatment. The analog also offers special possibilities for the prevention/treatment of hormone-sensitive cancers. The testosterone skeleton has important functionalities in the molecule that can act as a carbonyl component, an active methylene compound, α,β-unsaturated enone and tertiary hydroxyl group in various chemical reactions to access stereoisomeric steroidal compounds with potent activity. In addition, microbiological methods of synthesis and transformation of this hormone are presented.

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