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Paper | Special issue | Vol 84, No. 2, 2012, pp.983-1012
Published online, 7th October, 2011
DOI: 10.3987/COM-11-S(P)73
Synthesis of 8-Hydroxyisochromenes and 8-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

Two strategies were developed to prepare 8-hydroxyisocoumarins from substituted 3-ethoxycyclohex-2-en-1-ones. The key reactions in the first strategy were the cyclization of a 2-hydroxymethyl-3-ethynyl-cyclohex-2-en-1-one, followed by the aromatization of the resulting cyclohexenone-pyran intermediate. The second approach featured the reaction of 2-hydroxymethyl-3-vinyl-cyclohex-2-en-1-ones with DDQ to directly produce isocoumarins. This new two-step sequence was used to prepare oospolactone in 57% overall yield.