Acyloxy)alkoxy moiety as amino acids protecting group for the synthesis of (R,R)-2,7 diaminosuberic acid via RCM.

Adriano Mollica, Federica Feliciani, Azzurra Stefanucci, Evgeny A Fadeev, Francesco Pinnen

Faculty of Pharmacy, Department of Pharmaceutical Sciences, University of Chieti-Pescara G. d' Annunzio, Chieti, Italy. a.mollica@unich.it

Protein and peptide letters 2012 Dec

filter terms:

A new synthetic pathway is described to prepare asymmetrically protected 2,7-diaminosuberic acid. This strategy exploits (acyloxy)alkoxy promoiety as protecting group and RCM reaction using second generation Grubbs catalyst and provides the trans isomer of (2R,7R)-7-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(tert-butoxycarbonylamino)-8- methoxy-8-oxooct-4-enoic acid, which was in turn reduced to obtain (2R,7R)-7-(((9H-fluoren-9-yl)methoxy)carbonylamino)- 2-(tert-butoxycarbonylamino)-8-methoxy-8-oxooctanoic acid.

Citation

Adriano Mollica, Federica Feliciani, Azzurra Stefanucci, Evgeny A Fadeev, Francesco Pinnen. Acyloxy)alkoxy moiety as amino acids protecting group for the synthesis of (R,R)-2,7 diaminosuberic acid via RCM. Protein and peptide letters. 2012 Dec;19(12):1245-9