SYNTHESES OF OCTAHYDROQUINOLINE-N-OXIDES - HAPTENS DESIGNED TO ELICITCATALYTIC ANTIBODIES THAT CONTROL A TERPENOID-LIKE CASCADE CYCLIZATION

An efficient synthetic route to both cis-and trans-fused racemic 4a,6- dimethyloctahydroquinoline-N-oxides has been developed. These species were employed as haptens to elicit catalytic antibodies capable of con trolling the corresponding bicyclic hydrocarbon formation from linear quasi-triisoprenoid substrates. Temperature dependent NMR studies of c is-fused compounds proved the existence of two conformational states. Hapten 20b has elicited an antibody that efficiently catalyses a tande m cationic cyclisation leading to bridge-methylated decalins. (C) 1997 Elsevier Science Ltd.