Volume 28, Issue 13
Preparative Organic Chemistry
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ChemInform Abstract: Application of Chemical P-450 Model Systems to Studies on Drug Metabolism. Part 10. Novel Hydroxylactonization of γ,δ- and β,γ-Unsaturated Carboxylic Acids with an Iron Porphyrin- Iodosylbenzene System.

M. KOMURO

M. KOMURO

Fac. Pharm. Sci., Univ. Tokyo, Bunkyo, Tokyo 113, Japan

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T. HIGUCHI

T. HIGUCHI

Fac. Pharm. Sci., Univ. Tokyo, Bunkyo, Tokyo 113, Japan

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M. HIROBE

M. HIROBE

Fac. Pharm. Sci., Univ. Tokyo, Bunkyo, Tokyo 113, Japan

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First published: 04 August 2010

Abstract

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ChemInform Abstract

The title reaction is investigated with different kinds of unsaturated acids. The formation of hydroxy lactones is highly stereoselective. . beta.,γ-Unsaturated carboxylic acids are mainly decarboxylated. Lactone formation is observed in the case of iodomethacin, however with low yield and in a mixture of by-products. The lactones are also formed in the presence of microsomes. This metabolism is investigated and found to be cytochrome P-450 dependent.

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