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

✍ Scribed by Jens Hasserodt; Kim D. Janda

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 991 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00715-1

✦ Synopsis

An efficient synthetic route to both cis-and tram-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 c/s-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.