Further Explorations into the Synthesis of Dehydro??Hedione®

…, R Brauchli, JY de Saint Laumer

Index: Winter, Beat; Chapuis, Christian; Brauchli, Robert; De Saint Laumer, Jean-Yves Helvetica Chimica Acta, 2013 , vol. 96, # 2 p. 246 - 258

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Citation Number: 3

Abstract

Abstract Dehydrohedione (DHH) 1 may be obtained in 20% overall yield by a Reformatsky reaction with enone methyl ether 3b, followed by acidic workup of the crude reaction mixture. Alternatively, epoxidation (3-chloroperbenzoic acid, CH 2 Cl 2, 84% yield) of the tertiary allyl alcohol derivative 4 affords a 1: 2 mixture of 8a and 8b. The latter epoxy ester 8b may also be obtained stereoselectively either from 4 (t BuO 2 H,[Mo (CO) 6], 1, 2-dichloroethane, 70 ...