H. Gotanda et al., SYNTHESIS AND INSECTICIDAL ACTIVITY OF LIGNAN ANALOGS .8. CHROMANO-ANALOGS OF INSECTICIDAL NEOLIGNANS OF THE 1,4-BENZODIOXANE TYPE, Bioscience, biotechnology, and biochemistry, 57(6), 1993, pp. 884-889
Two haedoxan-analogs, 2H-chromen-6/7-yl]-3,7-dioxabicyclo[3.3.0]octane
s, were synthesized. They both had chromanyl groups instead of the -3-
(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-yl group of the haedoxan
molecule. In the synthesis, a (+/-)-(1S,2R*,5R*,6R*)-isomer was obtai
ned. An assay of these chromans indicated that the 1-oxygen atom of th
e 1,4-benzodioxane ring of haedoxans significantly contributed to thei
r insecticidal activity.