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Efficient and scalable synthesis of bardoxolone methyl (cddo-methyl ester).

Organic letters (2013-03-28)
Liangfeng Fu, Gordon W Gribble
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Oleanolic acid, ≥97%
Supelco
Oleanolic acid, analytical standard
Oleanolic acid, primary reference standard