Regioselectivity in the acid-catalyzed isomerization of 2-substituted 1, 4-dihydro-1, 4-epoxynaphthalenes

DG Batt, DG Jones, S La Greca

Index: Batt, Douglas G.; Jones, David G.; Greca, Susan La Journal of Organic Chemistry, 1991 , vol. 56, # 23 p. 6704 - 6708

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Citation Number: 40

Abstract

In the course of examining the structure-activity relationships of a series of 5-lipoxygenase- inhibitory 2-(arylmethyl)-1-naphthols,'we wanted to prepare 8-substituted analogues, hoping that greater metabolic stability would result from steric hinderance near the hydroxyl group. Synthetic approaches involving elaboration of preexisting 2-or 8-substituted naphthols were excluded because of potential difficulties arising from peri interactions, which can induce ...