An improved approach for the preparation of enantiopure 3,4-bis-tert-butoxypyrroline N-oxides is presented. Etherification of 1-benzylpyrrolidine-3,4-diol with tBuOAc/HClO4 and subsequent N-debenzylation and pyrrolidine oxidation with oxone affords the cyclic nitrone reliably and in superior yield. The enantiomer derived from D-tartaric acid was exploited in a modified synthesis of (-)-7S-OH-lentiginosine. The activity of this trihydroxy indolizidine in inducing the apoptosis of tumour cell lines of lymphoid and epithelial origin is examined.

(−)-(1R,2R,7S,8aR)-1,2,7-Trihydroxyindolizidine ((−)-7S-OH-Lentiginosine): Synthesis and Proapoptotic Activity

MASTINO, Antonio
2012

Abstract

An improved approach for the preparation of enantiopure 3,4-bis-tert-butoxypyrroline N-oxides is presented. Etherification of 1-benzylpyrrolidine-3,4-diol with tBuOAc/HClO4 and subsequent N-debenzylation and pyrrolidine oxidation with oxone affords the cyclic nitrone reliably and in superior yield. The enantiomer derived from D-tartaric acid was exploited in a modified synthesis of (-)-7S-OH-lentiginosine. The activity of this trihydroxy indolizidine in inducing the apoptosis of tumour cell lines of lymphoid and epithelial origin is examined.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11570/2008024
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