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Journal of Lipid Research, Vol 29, 1097-1101, Copyright © 1988 by Lipid Research, Inc.

ARTICLES

A facile one-step synthesis of delta 1,4-3-keto bile acid esters by iodoxybenzene and benzeneselenic anhydride

T Iida, T Shinohara, J Goto, T Nambara and FC Chang
College of Engineering, Nihon University, Fukushima-ken, Japan.

A facile one-step conversion of stereoisomeric methyl 3- hydroxycholanoates to 1,4-dien-3-one, by treatment in boiling toluene with iodoxybenzene catalyzed by benzeneselenic anhydride, is described. The direct oxidation-dehydrogenation at C-3 is applicable to other cholanoates (hyodeoxycholic, chenodeoxycholic, ursodeoxycholic, deoxycholic, and cholic) when the hydroxyl groups at C-6, C-7, or C-12 are protected. Without protection at C-6 and C-7, the products from hyodeoxycholic, chenodeoxycholic, ursodeoxycholic, and cholic esters are complex mixtures, whereas, methyl deoxycholate yields the 1,4-dien- 3,12-dione cleanly.
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