One-pot synthesis of highly functionalized morphans from C-glycosides

Highly functionalized morphan derivatives were synthesized from nitroalkene 2′-(oxoalkyl)-C-glycosides by a tandem reaction that created three (two C–N and one C–C) new bonds and four stereogenic centers in a one-pot procedure under very mild conditions without the use of expensive reagents. The transformation was achieved from a β-elimination/Michael addition cascade, followed by Michael addition of the amine and intramolecular enamination. In the presence of sodium cyanoborohydride the iminium intermediate was reduced in situ to afford the desired morphans.

Figure optionsDownload as PowerPoint slide