Synthesis of arylnaphthalene lignans

ORGN 159

Shingiria Chirisa, chirisa.2@wright.edu and William A. Feld, william.feld@wright.edu. Department of Chemistry, Wright State University, 3640 Col Glenn Hwy, Dayton, OH 45435
Haplomyrtin is an arylnaphthalene lignan from a perennial herb, Haplophyllum Myrtifolium, endemic to Turkey. The total synthesis of Haplomyrtin involves nine steps with eight isolable products using vanillin and piperonal as starting materials. The key steps in the sequence are the acid catalyzed formation of an aryl substituted benzofuran trapped by a Diels-Alder reaction with dimethyl acetylenedicarboxylate and the regioselective reduction of a diester to give the required lactone. Structural derivatives with various aryl (Ar) substituents will also be discussed.