Studies related to the synthesis of dimethyl tetracyclo[5.2.1.02,6.03,8]decane-7,8-dicarboxylate

Abstract

A synthesis of dimethyl tetracyclo[5.2.1.02,6.03,8]decane-7,8-dicarboxylate, 3, whose key step implies the formation of the C1—C2 bond by regioselective intramolecular C—H insertion of a carbene generated from dimethyl (1R,2S,6R,7S)-10-oxotricyclo[5.2.1.02,6]decane-2,6-dicarboxylate, 1 via its tosylhydrazone, is described. Attempts to synthesize diester 3 or compounds containing its carbon skeleton, by forming the same C—C bond, starting from dimethyl (1R,2S,6R,7S)-4-oxotricyclo[5.2.1.02,6]decane-2,6-dicarboxylate, 2, or the corresponding anhydride, 13, are also included.