One of the main functions of iminosugars is they inhibit enzymes called glycosidases which break down oligo- and polysaccharides into smaller sugars.  Inhibiting glycosidases is in plants plant defense mechanisms and in tumor reduction.  In our research, we used organic synthesis to synthesize the iminosugar Lentiginosine. The first three steps of the synthesis involves the well-established conversion of 4,6-O-benzylidine-a-D-glucopyranoside 1  into the protected 6-iodo derivative 4 .  Then, the synthesis branches off into two separate pathways that involve a reductive amination, a ring closing metathesis, and second cyclization through an SN2 reaction.  The second is similar to the first, but avoids the formation of the nine-membered ring because of the low yield.  The problem with this new approach is the metathesis of the divinyl amine may not be possible due to the amine interfering with the Ru catalyst. Due to time restraints, Lentiginosine was not made.

Synthesis of lentiginosine from D–glucose

243rd National Meeting (2012)

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