Synthesis of diacetal trioxa-cage compounds via reaction of bicycle [2.2.1]heptenes and bicyclo[2.2.2]octenes with dimethyldioxirane

Abstract

A new entry for the synthesis of diacetal trioxa-cage compounds via oxirane-induced sequential cyclization reaction of 2,3-bis-endo-diacylbicyclo[2.2.1]-5-heptenes and 2,3-bis-endo-diacylbicyclo[2.2.2]-5-octenes is reported. In the case of bicyclo[2.2.2]octenes, sequential cyclization reaction induced by iodine as electrophile failed. We have also demonstrated that dimethyldioxirane can selectively oxidize hemiacetals to give lactones with the secondary hydroxy group intact. (C) 2000 Elsevier Science Ltd. All rights reserved.