The study of alkoxide-promoted enyne-allene cyclizations: Next generation isolated alkenes

ORGN 62

Michelle K. Waddell and Mark A. Lipton. Department of Chemistry, Purdue University, 560 Oval Drive, P.O. Box 805, West Lafayette, IN 47907-2084
In our research group we have designed a simple model system of the neocarzinostatin A chromophore that consists of a carbocyclic core bearing an oxyanion-substituted enyne-allene moiety. The cyclization of oxyanion-substituted benzannulated enyne-allenes was previously studied in our group and was shown to result in C2-C6 cyclization rather than the expected C2-C7 (Myers) cyclization. In our current study, the cyclization of an oxyanion-subsitituted enyne-allene fused to a cyclohexene core is examined. The cyclization products of this compound will be compared with those of its cyclopentannulated and benzannulated analogues.