HETEROCYCLES

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■ Synthesis and Characterization of a Novel 6-Heteroaryl-3,6-dihydro-2H-pyran-2-acetic Acid

Gerald E. Stokker and Steven M. Pitzenberger

*Department of Medicinal Chemistry, Merck Sharp and Dohme Research Laboratories, West Point, PA 19486, U.S.A.

Abstract

Cis and trans-6-[2-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]ethenyl]-3,4, 5,6-tetrahydro-4-hydroxy-2H-pyran-2dne (1b and 1a) rearrange under mildly acidic conditions giving only cis-6-[3-(4-fluorophenyl)-l-(l-methylethyl)-1H-indol-2-yl]-3,6-dihydro-2H-pyran-2-acetic acid (3). A mechanism is proposed for the acid catalyzed rearrangement.