Synthesis and Pseudomonas lipase inhibition study of stereoisomers of decahydro-2-naphthyl-N-n-butylcarbamate

(2s,4ar,8as)-cis,cis-,(2r,4as,8ar)-cis,cis-,rac-cis,cis-,and rac-trans,cis-decahydro-2-naphthyl-n-n-butylcarbamates are synthesized from condensation of (2s,4ar,8as)-cis,cis-,(2r,4as,8ar)-cis,cis-,rac-cis,cis-,and rac-trans,cisdecahydro-2-naphthols,respectively,with n-butyl isocyanate in the presence of triethylamine in dichloromethane. optically pure (2s,4ar,8as)-(-)-and (2r,4as,8ar)-(+)-cis,cis-decahydro-2-naphthols are resolved by the porcine pancreatic lipase-catalyzed acetylation of decahydro-2-naphthols with vinyl acetate in t-butyl methyl ether. absolute configurations of (2s,4ar,8as)-(-)-and (2r,4as,8ar)-(+)-cis,cis-decahydro-2-naphthols are determined from the 19f nmr spectra of their mosher's ester derivatives. (2s,4ar,8ar)-trans,cis-and (2r,4as,8as)-trans,cis-decahydro-2- naphthols can't be resolved from the porcine pancreatic lipase-catalyzed acetylation of decahydro-2-naphthols with vinyl acetate in t-butyl methyl ether. for the inhibitory potency of pseudomonas lipase,(2s,4ar,8as)-cis,cis- decahydro-2-naphthyl-n-n-butylcarbamate is 3.5 times more potent than (2r,4as,8ar)-cis,cis-decahydro-2-naphthyl-n-n-butylcarbamate; racemic cis,cis-decahydro-2-naphthyl-n-n-butylcarbamate is about the same with trans,cis-decahydro-2-naphthyl-n-n-butylcarbamate. these inhibitors also show similar effects on porcine pancreatic lipase. © 2011 bentham science publishers.