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Communication | Special issue | Vol 103, No. 2, 2021, pp.707-713
Published online, 1st February, 2021
DOI: 10.3987/COM-20-S(K)69
IBX Oxidations for the Synthesis of Substituted 2H-Pyrans

David R. Williams,* Seth A. Bawel, Nazanin Haddadpour, and Sarah Maier

*Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, IN 47405-7102, U.S.A.

Abstract

Facile oxidation of highly substituted 3,5-hexadien-1-ols using 3-iodoxybenzoic acid (IBX) in DMSO has resulted in a one-pot preparation of 2,3,4,6-tetrasubstituted 2H-pyrans. Cycloisomerizations of the 1-oxatriene moiety, produced in the oxidation, spontaneously occur via a disrotatory oxa-electrocyclization. The 2H-pyran products of Table 1 features three differentiated carbonyl substituents.