Volume 27, Issue 23
Natural Products
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ChemInform Abstract: The Cyanide-Catalyzed Isomerization of Enol Esters Derived from Cyclic 1,3-Diketones.

I. FLORES MONTES

I. FLORES MONTES

Dep. Chim. Org., Univ. Geneve, CH-1211 Geneve 4, Switz.

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U. BURGER

U. BURGER

Dep. Chim. Org., Univ. Geneve, CH-1211 Geneve 4, Switz.

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First published: June 4, 1996

Abstract

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ChemInform Abstract

In connection with synthetic studies on the antibiotic pyoluteorin the title reaction is investigated. Thus, acylation of the diketone (I) with aliphatic acyl chlorides, e.g. (II), gives an intermediate O- acylation product which rearranges via the formation of acyl cyanides to the C-acylation product (III). However, application of the sequence to acid chloride (IV) takes another course. The desired C-acylation product (VIII) is directly obtained from (I) and the acyl cyanide (VII) . The aromatization of (VIII) to the corresponding resorcinol, a precursor of pyoluteorin, is not achieved (some yields not given).

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