Synthesis of new aza-analogs of staurosporine, K-252a and rebeccamycin by nucleophilic opening of C2-symmetric bis-aziridines

Sandrine Delarue-Cochin, Isabelle McCort-Tranchepain
2009 Organic and biomolecular chemistry  
The 1,2-O-isopropylidene and 1,2-O-dibenzyloxy-NH bis-aziridines, precursors of all the N-protected bis-aziridines, were obtained according to our previous procedure. 1 Bis-indolylmaleimide 5d and indolocarbazole 6b were synthesized according to classical procedures. 2 General procedure for the synthesis of 9a-d and 10a-c. To a solution of crude NH bis-aziridine (1.0 eq) in DMF (0.4 M) cooled at -15 °C, were slowly added Et 3 N (15.0 eq) and a solution of either TsCl, SES-Cl, Mts-Cl, (2.5 eq)
more » ... Boc 2 O (1.0 eq) in DMF (1 M). After stirring for 4 h at this temperature, the mixture was poured in H 2 O and extracted with Et 2 O. The organic layers were then dried over MgSO 4 , filtered and concentrated. The residue was purified by column chromatography (cyclohexane/EtOAc/NH 4 OH: 85/15/1).
doi:10.1039/b815737e pmid:19194586 fatcat:njssbjw4j5h2hg6yok3o7465da