Iodine-induced cyclization reaction of endo-thioester substituted norbornenes followed by methylthio group rearrangement

Abstract

Treatment of the endo-thioester group substituted norbornenes 3a-3d with iodine in aqueous tetrahydrofuran at 25 degrees C gave the novel methylthio group rearranged lactonization products 4a-4d in 80% yields; iodolactonization reaction of 9 was applied to the synthesis of novel diacetal trioxa-cage compound 13. Copyright (C) 1996 Elsevier Science Ltd