Synthesis of a Model Hapten with Cyclohexanediol and &α-Methylene-&γ-butyrolactone Groups, a Synthetic Analogue of Poison Ivy and Tulipalin Allergens Connected with a Carbon Chain

Article abstract of DOI:10.1021/jo00247a014

Potential skin sensitizers 1 and 1* with two different haptenic ends, (a) a cyclohexanediol group (saturated poison ivy analogue ) and (b) an α-methylene-γ-butyrolactone moiety (tulipalin A), separated by a nine carbon atoms chain containing a double bond have been prepared.The trans, trans relationship in the substituted cyclohexanediol was secured by a tandem Michael addition-hydroboration reaction.Contrary to an earlier example of a double-headed hapten containing pyrocatechol and α-methylene-γ-butyrolactone ends, the cyclohexanediol-α-methylene-γ-butyrolactone does not show any tolerance induction to the α-methylene-γ-butyrolactone end.It therefore seems that induction of tolerance as well as sensitization requires the formation of covalent bond with a protein carrier.