The synthesis of 7-halo-1,2-dihydroxyindolizidines (7-halolentiginosines) starting from suitable protected 1,2,7-trihydroxyindolizidines (7-hydroxylentiginosines) has been studied. The results indicate a high propensity of the substrates to undergo fragmentation processes under standard halogenations conditions. The analysis of the products allowed an unprecedented full rationalization of Grob fragmentations processes in 7-substituted 1,2-alkoxyindolizidines. Under optimized Appel reaction conditions 7-chloro- and 7-iodolentiginosines could be exclusively achieved (89e100% yields), whereas fluoruration was extremely sluggish and the 7-fluoro derivative was formed in only 19% through a twostep protocol. Biological assays proved that 7-fluoro- and 7-iodolentiginosines are endowed with proapoptotic activity analogously to ()-lentiginosine and 7-hydroxylentiginosine.

Vurchio, C., Cordero, F., Faggi, C., Macchi, B., Frezza, C., Grelli, S., et al. (2015). Approaches towards the synthesis of 7-halo-1,2-dihydroxyindolizidines (7-halolentiginosines) thwarting Grob fragmentation processes. TETRAHEDRON, 71, 5806-5813 [10.1016/j.tet.2015.03.108].

Approaches towards the synthesis of 7-halo-1,2-dihydroxyindolizidines (7-halolentiginosines) thwarting Grob fragmentation processes

MACCHI, BEATRICE;GRELLI, SANDRO;
2015

Abstract

The synthesis of 7-halo-1,2-dihydroxyindolizidines (7-halolentiginosines) starting from suitable protected 1,2,7-trihydroxyindolizidines (7-hydroxylentiginosines) has been studied. The results indicate a high propensity of the substrates to undergo fragmentation processes under standard halogenations conditions. The analysis of the products allowed an unprecedented full rationalization of Grob fragmentations processes in 7-substituted 1,2-alkoxyindolizidines. Under optimized Appel reaction conditions 7-chloro- and 7-iodolentiginosines could be exclusively achieved (89e100% yields), whereas fluoruration was extremely sluggish and the 7-fluoro derivative was formed in only 19% through a twostep protocol. Biological assays proved that 7-fluoro- and 7-iodolentiginosines are endowed with proapoptotic activity analogously to ()-lentiginosine and 7-hydroxylentiginosine.
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore CHIM/06 - Chimica Organica
Settore BIO/14
English
Con Impact Factor ISI
Apoptosis Azasugar Fragmentation reaction Halogenation Indolizidine
Vurchio, C., Cordero, F., Faggi, C., Macchi, B., Frezza, C., Grelli, S., et al. (2015). Approaches towards the synthesis of 7-halo-1,2-dihydroxyindolizidines (7-halolentiginosines) thwarting Grob fragmentation processes. TETRAHEDRON, 71, 5806-5813 [10.1016/j.tet.2015.03.108].
Vurchio, C; Cordero, F; Faggi, C; Macchi, B; Frezza, C; Grelli, S; Brandi, A
Articolo su rivista
File in questo prodotto:
File Dimensione Formato  
Vurchio et al Tetrahedron 2105.pdf

non disponibili

Descrizione: articolo principale
Licenza: Copyright dell'editore
Dimensione 1 MB
Formato Adobe PDF
1 MB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/113697
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 5
  • ???jsp.display-item.citation.isi??? 4
social impact