page_title: Azastene
section_title: Synthesis
hierarchical_section_title: Azastene / Synthesis
caption_attribution_description: English: Gordon O. Potts, Sterling Drug Inc. U.S. Patent 3,966,926 (1976).
context_page_description: Azastene is a steroidogenesis inhibitor described as a contraceptive, luteolytic, and abortifacient which was never marketed. It acts as a competitive inhibitor of 3β-hydroxysteroid dehydrogenase, and thereby inhibiting the formation of progesterone, corticosteroids, androgens, and estrogens. Due to inhibition of corticosteroid synthesis, azastene is immunosuppressive.
context_section_description: One synthesis of this compound involves initial alkylation of methyl testosterone by means of strong base and methyl iodide to afford the 4,4-dimethyl derivative. Formylation with alkoxide and methyl formate leads to the 2-hydroxymethyl derivative. Reaction of this last with hydroxylamine leads to formation of an isoxazole ring. There is then obtained azastene.
caption: Azastene synthesis:[5]
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