Stereochemistry of Pyrethrosin, Cyclopyrethrosin Acetate and Isocyclopyrethrosin Acetate

Abstract

The acid cyclization product from pyrethrosin has been proved to be a (1:1)-mixture of cyclopyrethrosin acetate containing a Δ³⁽⁴⁾-double bond and isocyclopyrethrosin acetate with a Δ⁴⁽¹⁵⁾-double bond through the reinvestigation. NMR and ORD studies on their derivatives led us to assign revised stereochemistry to pyrethrosin and its related compounds.