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.

Cordero, F., Bonanno, P., Khairnar, B., Cardona, F., Brandi, A., Macchi, B., et al. (2012). (-)-(1R,2R,7S,8aR)-1,2,7-trihydroxyindolizidine ((-)-7S-OH-lentiginosine): Synthesis and proapoptotic activity. CHEMPLUSCHEM, 77(3), 224-233 [10.1002/cplu.201100069].

(-)-(1R,2R,7S,8aR)-1,2,7-trihydroxyindolizidine ((-)-7S-OH-lentiginosine): Synthesis and proapoptotic activity

MACCHI, BEATRICE;MINUTOLO, ANTONELLA;GRELLI, SANDRO;
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.
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore BIO/14
Settore CHIM/06 - Chimica Organica
English
Con Impact Factor ISI
settori disciplinari coinvolti: chim03 e Bio14
Cordero, F., Bonanno, P., Khairnar, B., Cardona, F., Brandi, A., Macchi, B., et al. (2012). (-)-(1R,2R,7S,8aR)-1,2,7-trihydroxyindolizidine ((-)-7S-OH-lentiginosine): Synthesis and proapoptotic activity. CHEMPLUSCHEM, 77(3), 224-233 [10.1002/cplu.201100069].
Cordero, F; Bonanno, P; Khairnar, B; Cardona, F; Brandi, A; Macchi, B; Minutolo, A; Grelli, S; Mastino, A
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/64685
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