The de novo synthesis of piperidine nucleosides from our homologating agent 5,6-dihydro-1,4-dithiin is herein reported. The structure and conformation of nucleosides were conceived to faithfully resemble the well-known nucleoside drugs Immucillins H and A in their bioactive conformation. NMR analysis of the synthesized compounds confirmed that they adopt an iminosugar conformation bearing the nucleobases and the hydroxyl groups in the appropriate orientation.
Keywords: biomimetics; conformationally restricted nucleosides; de novo synthesis; iminosugars; immucillins; nucleoside analogues; piperidine nucleosides; polymer-supported triphenyl phosphine.