Efficient and Scalable Synthesis of Bardoxolone Methyl (CDDO-methyl Ester)

Bardoxolone methyl (2-cyano-3,12-dioxooleane-1,9(11)-dien-28-oic acid methyl ester; CDDO-Me) (1), a synthetic oleanane triterpenoid with highly potent anti-inflammatory activity (levels below 1 nM), has completed a successful phase I clinical trial for the treatment of cancer and a successful phase...

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Veröffentlicht in:	Organic letters 2013-04, Vol.15 (7), p.1622-1625
Hauptverfasser:	Fu, Liangfeng, Gribble, Gordon W
Format:	Artikel
Sprache:	eng
Schlagworte:	Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - pharmacology Chromatography Diabetes Mellitus, Type 2 - drug therapy Esters Humans Molecular Structure Oleanolic Acid - analogs & derivatives Oleanolic Acid - chemical synthesis Oleanolic Acid - chemistry Oleanolic Acid - pharmacology Renal Insufficiency, Chronic - drug therapy
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Zusammenfassung:	Bardoxolone methyl (2-cyano-3,12-dioxooleane-1,9(11)-dien-28-oic acid methyl ester; CDDO-Me) (1), a synthetic oleanane triterpenoid with highly potent anti-inflammatory activity (levels below 1 nM), has completed a successful phase I clinical trial for the treatment of cancer and a successful phase II trial for the treatment of chronic kidney disease in type 2 diabetes patients. Our synthesis of bardoxolone methyl (1) proceeds in ∼50% overall yield in five steps from oleanolic acid (2), requires only one to two chromatographic purifications, and can provide gram quantities of 1.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol400399x