Stereocontrolled synthesis of the oxabicyclo[2.2.1]heptane segment of solanoeclepin A

摘要

An asymmetric synthesis of the oxabicyclo[2.2.1]heptane segment of Solanoeclepin A, which shows significant hatch-stimulating activity for the potato cyst nematode, is described. The oxabicyclo framework was constructed by iodoetherification with bis(collidine)iodine(I) hexafluorophosphate in acetonitrile. The oxabicyclo segment was further synthesized by the following stereoselective dihydroxylation and dimethyl group introduction.