THE SYNTHESIS OF 2,3-DISUBSTITUTED CYCLOPENTENONES USING THE RAMBERG-BAECKLUND REACTION IN CONJUNCTION WITH ORGANOCOPPER CHEMISTRY

Article abstract of DOI:10.1016/0040-4020(89)80073-0

An improved synthetic procedure is described for the preparation of 2,3-dialkylated 2,3-dihydrothiin-4-ones using organocopper chemistry.The utility of these, and the corresponding saturated compounds for the synthesis of Δ³- and Δ²-2,3-disubstituted cyclopentenones via the Ramberg-Baecklund reaction is discussed.The application of this methodology to a formal total synthesis of the antimicrobial natural product tetrahydrodicranenone B is described.