Tetrahedron

Synthesis of (9E)-isoambrettolide, a macrocyclic musk compound, using the effective lactonization promoted by symmetric benzoic anhydrides with basic catalysts

I Shiina, M Hashizume

Index: Shiina, Isamu; Hashizume, Minako Tetrahedron, 2006 , vol. 62, # 33 p. 7934 - 7939

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Citation Number: 27

Abstract

Two alternative methods for the synthesis of (9E)-isoambrettolide are established via the rapid lactonization of the free threo-aleuritic acid or its protected seco-acid using substituted benzoic anhydrides with basic catalysts. The most efficient lactonization of the threo-aleuritic acid is performed using 2-methyl-6-nitrobenzoic anhydride (MNBA) with a catalytic amount of 4-dimethylaminopyridine N-oxide (DMAPO).