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
2012-01-01
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.File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
