Tetrahedron

Stereocontrolled synthesis of highly functionalized cyclohexenes. A short synthesis of a chorismic acid precursor

GH Posner, TD Nelson

Index: Posner, Gary H.; Nelson, Todd D. Tetrahedron, 1990 , vol. 46, # 13/14 p. 4573 - 4586

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Citation Number: 41

Abstract

A convenient and mild thermal procedure has been developed for stereoselective 2+ 4- cycloadditions of electron-rich 1, 2-dioxygenated olefins 7 to electron-deficient 3-sulfonyl-2- pyrone 6 allowing isolation of the structurally and stereochemically rich initial bicyclic adducts 8. These bicyclic adducts are shown to be useful building units as exemplified by a very short and high-yield preparation of a chorismic acid precursor.