Design and synthesis of novel, pseudo C2 symmetric inhibitors of HIV protease

A novel series of chain-extended, pseudo C2 symmetric 1,5-diaminoalcohol analogs was designed and synthesized using an efficient nitroaldol condensation mediated by triethylsilyl triflate and TBAF.xH2O. Prototypical acyclic compounds harboring a central spirolactam or a nitro group, and amide variants of an off-center 1,5-diaminoalcohol analog were synthesized and their activities against HIV protease evaluated.