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Paper | Special issue | Vol 84, No. 2, 2012, pp.963-982
Published online, 7th October, 2011
DOI: 10.3987/COM-11-S(P)78
Synthesis of 6-Hydroxyisochromenes and 6-Hydroxyisocoumarins from 3-Ethoxycyclohex-2-en-1-one

George Majetich* and Jeremy L. Grove

*Department of Chemsitry, The University of Georgia, Athens, Georgia 30602, U.S.A.

Abstract

The synthesis of alkylated 6-hydroxyisochromenes and alkylated 6-hydroxyisocoumarins from 3-ethoxycyclohex-2-en-1-one was developed. The key reaction features a novel intramolecular hydroalkoxylation of a cyclohex-2-en-3-yn-1-one to assemble the dihydropyran moiety. Aromatization of the cyclohex-2-en-1-one ring used a selenylation/oxidative elimination sequence. The isochromenes were oxidized to their isocoumarin analogues using DDQ.