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

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
46
Identifiers
DOI: 10.1016/s0040-4020(01)85582-4
Disciplines
  • Chemistry

Abstract

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.

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