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Azastene, also known as 4,4,17α-trimethylandrosta-2,5-dieno(2,3-d)isoxazol-17β-ol, is a chemical that modulates 3β-hydroxysteroid dehydrogenase activity.
Synthesis
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.
References
Azastene Wikipedia(Text) CC BY-SA