NOVEL HALOGEN-SUBSTITUTED CYCLOHEXA-Z4-DIENONES AS DIENES FOR THE INTER MOLECULAR DIELS-ALDER REACTION. SYNTHESIS AND CHARACTERIZATION OF BICYCLO[2.2.2.] OCTENONE DERIVATIVES

Abstract

Utilization of easily available and less expensive starting materials for the rapid construction of complex molecules with defined stereochemistry is an exciting and challenge for the synthetic organic chemists. In this connection the synthesis of bicyclo[2.2.2]octenone derivatives using 4-halo-2-methoxyphenol as an inexpensive starting material is described. The synthesis of bicyclo[2.2.2]octenone derivatives from the reactions of 4-halo-2- methoxyphenol (217, 221) with methyl acrylate and methyl methacrylate have been carried out using hypervalent iodine reagent diacetoxyiodobenzene. Bicyclo[2.2.2]octenone derivatives that are potential intermediate for the total synthesis of natural products are obtained.