Syntheses of octahydroquinoline-N-oxides: Haptens designed to elicit catalytic antibodies that control a terpenoid-like cascade cyclisation

Article abstract of DOI:10.1016/S0040-4020(97)00715-1

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 controlling the corresponding bicyclic hydrocarbon formation from linear quasi-triisoprenoid substrates. Temperature dependent NMR studies of cis-fused compounds proved the existence of two conformational states. Hapten 20b has elicited an antibody that efficiently catalyses a tandem cationic cyclisation leading to bridge-methylated decalins.