A short synthesis of troglitazone: An antidiabetic drug for treating insulin resistance

Troglitazone was obtained in 5 steps from 4-bromo-1,1-dimethoxy-3-methylbut-2-ene with an overall yield of 7.5%. The formation of the chromane ring was achieved by condensing an unsaturated acetal with trimethylhydroquinone in the presence of bis(trifluoromethylsulfonyl)imide. The synthesis of trogl...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 1999-12, Vol.9 (24), p.3439-3440
Hauptverfasser:	Cossy, Janine, Menciu, Cecilia, Rakotoarisoa, Haja, Kahn, Philippe H., Desmurs, Jean-Roger
Format:	Artikel
Sprache:	eng
Schlagworte:	Biological and medical sciences Chemistry Chromans - chemical synthesis Exact sciences and technology General and cellular metabolism. Vitamins Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Hypoglycemic Agents - chemical synthesis Insulin Resistance Medical sciences Organic chemistry Pharmacology. Drug treatments Preparations and properties Thiazoles - chemical synthesis Thiazolidinediones Troglitazone
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Beschreibung
Zusammenfassung:	Troglitazone was obtained in 5 steps from 4-bromo-1,1-dimethoxy-3-methylbut-2-ene with an overall yield of 7.5%. The formation of the chromane ring was achieved by condensing an unsaturated acetal with trimethylhydroquinone in the presence of bis(trifluoromethylsulfonyl)imide. The synthesis of troglitazone was achieved in 5 steps from acetal 1 with an overall yield of 7.5%.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/S0960-894X(99)00630-7