Tetrahedron

The intramolecular enyne diels-alder reaction. Stereoselective construction of tricyclic dioxadienones and mechanistic outline

…, D Krumwiede, B Mucha, HH Oehlerking, GW Prahst

Index: Hoffmann, H. M. R.; Krumwiede, D.; Mucha, B.; Oehlerking, H. H.; Prahst, G. W. Tetrahedron, 1993 , vol. 49, # 40 p. 8999 - 9018

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Citation Number: 21

Abstract

4-Methylpent-4-en-2-yn-1-ols and 6-hydroxy-2, 3-dihydro-6H-pyran-3-ones are condensed in different ways to a series of tricyclic dioxadienones which contain the basic framework of the cadlinolides. A mechanism of the intramolecular enyne-ene cycloisomerization and the origin of the resulting type I and type II dienes is proposed.