[reaction: see text] A stereocontrolled synthesis of the DE fragment (2) of the marine alkaloid upenamide (1) is described. The synthesis proceeds in 12 steps from caprolactone (10) and 20-25% overall yield.

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N,N-Bis[(benzotriazol-1-yl)methyl]benzylamines and N,N-bis[(benzotriazol-1-yl)methyl](p-N',N'-dimethylphenyl)amine on reaction with allyltrimethylsilanes yielded substituted piperidines. Other N,N-bis[(benzotriazol-1-yl)methyl]anilines (unsubstituted and p-CH(3), OCH(3), Cl) gave julolidines (2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij] quinoline).

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