Structure of the Novel Insecticidal Sesquilignan, Haedoxan A

Abstract
Haedoxan A, a new insecticidal sesquilignan, was isolated from the root of Hae-doku-sou, Phryma leptostachya L., and the structure was elucidated as a 1-hydroxy-2-[(2,6-dimethoxy-3,4-methylenedioxyphenyl)oxy]-6-[6′-methoxy-2′-methoxymethyl-3′-(3,4-methylenedioxyphenyl)-2′,3′-dihydro-r,4′-benzodioxin-7′-yl]-3,7-dioxabicyclo[3.3.0]octane on the basis of spectroscopic and chemical information involving syntheses of its partial structures. Its relative stereochemistry was revealed to be (1S*, 2R*, 5R*, 6S*, 2′ R*, 3′ R*) or (1S*, 2R*, 5S*, 6S*, 2′ S*, 3′ S*).

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