New syntheses of dillapiol [4, 5-dimethoxy-6-(2-propenyl)-1, 3-benzodioxole], its 4-methylthio and other analogs

SL Majerus, N Alibhai, S Tripathy…

Index: Majerus, Sherry L.; Alibhai, Najma; Tripathy, Sasmita; Durst, Tony Canadian Journal of Chemistry, 2000 , vol. 78, # 10 p. 1345 - 1355

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Citation Number: 5

Abstract

Three syntheses of the natural synergist dillapiol from the natural, commercially available sesamol as starting material, are described. A major difference between these is the order of introduction of the additional methoxy and allyl substituents. In one of the syntheses, a formyl group is introduced at C4 via an electrophilic aromatic substitution reaction and then converted into the methoxy group using a Baeyer-Villiger reaction and subsequent ...