A Stereoselective Synthesis of Lentiginosine
Franca M Cordero1, Carolina Vurchio1, Alberto Brandi1
1Dipartimento di Chimica "Ugo Schiff", Università di Firenze , via della Lastruccia 13, 50019 Sesto Fiorentino (FI), Italy.
Abstract:
A concise stereoselective synthesis of (-)-lentiginosine, an iminosugar endowed with an interesting proapoptotic activity, has been accomplished using an enantiopure pyrroline N-oxide building block derived from d-tartaric acid. Key steps are a totally diastereoselective nucleophilic addition to the cyclic nitrone followed by a combination of two simultaneous and two tandem reactions occurring under the same conditions in a single laboratory operation. Natural (+)-lentiginosine can be synthesized by the same method but starting from l-tartaric acid.
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