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| - Formation of Bridge-Methylated Decalins byAntibody-Catalyzed Tandem Cationic Cyclization
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| - We report the antibody catalysis of an electrophilic tandem ringforming process that yields a bicyclicring system at neutral pH. Three closely related decalin systemsthat represent rings A and B of the steroid nucleusaccount for 50% of the overall products. The linear dienesubstrate has been designed to mimic the first twoisopreneunits of 2,3-oxidosqualene, where the epoxide oxygen has beensubstituted by an arylsulfonate as leaving group.The hapten is based on a decahydroquinoline system with anN-oxide functionality as the key structure to elicitacombining site architecture capable of promoting leaving group release.The kcat for the formation of sulfonicacidin the catalyzed reaction was determined to be 0.021min-1. The efficiency of theantibody-catalyzed process isunderscored by the fact that the bicyclic products are not formed inthe absence of the antibody catalyst under ourmild conditions.
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