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

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 t BuOAc/HClO 4 and subsequent N‐debenzylation and pyrrolidine oxidation with oxone affords the cyclic nitrone reliably and in su...

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Published inChemPlusChem (Weinheim, Germany) Vol. 77; no. 3; pp. 224 - 233
Main Authors Cordero, Franca M., Bonanno, Paola, Khairnar, Bhushan B., Cardona, Francesca, Brandi, Alberto, Macchi, Beatrice, Minutolo, Antonella, Grelli, Sandro, Mastino, Antonio
Format Journal Article
LanguageEnglish
Published 01.03.2012
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Summary: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 t BuOAc/HClO 4 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 (−)‐7 S ‐OH‐lentiginosine. The activity of this trihydroxy indolizidine in inducing the apoptosis of tumour cell lines of lymphoid and epithelial origin is examined.
ISSN:2192-6506
2192-6506
DOI:10.1002/cplu.201100069