Synthesis of the Right-Hand Substructure of Solanoeclepin A

Abstract

A synthesis of the right-hand substructure 7 of solanoeclepin A (1), the most active natural hatching agent of potatocyst nematodes, was approached by an intramolecular [2+2] photocycloaddition. The construction of the strained bicyclo[2.1.1]hexane skeleton was achieved in five steps from dioxenone 9. A Simmons−Smith cyclopropanation enabled the installation of the required cyclopropane. Finally, a TPAP oxidation allowed the smooth formation of the strained cyclobutanone moiety.