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 / F. M. Cordero; P. Bonanno; B. B. Khairnar; F. Cardona; A. Brandi; B. Macchi; A. Minutolo; S. Grelli; A. Mastino. - In: CHEMPLUSCHEM. - ISSN 2192-6506. - ELETTRONICO. - 77:(2012), pp. 224-233. [10.1002/cplu.201100069]

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

CORDERO, FRANCA MARIA;BONANNO, PAOLA;KHAIRNAR, BHUSHAN BALASAHEB;CARDONA, FRANCESCA;BRANDI, ALBERTO;
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.
2012
77
224
233
F. M. Cordero; P. Bonanno; B. B. Khairnar; F. Cardona; A. Brandi; B. Macchi; A. Minutolo; S. Grelli; A. Mastino
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/593109
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