- Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation.
Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation.
Bioorganic & medicinal chemistry letters (2011-07-16)
Sergey Vshyvenko, Jon Scattolon, Tomas Hudlicky, Anntherese E Romero, Alexander Kornienko
PMID21757350
ABSTRACT
The synthesis of two C-1 analogues of pancratistatin has been accomplished in 17 steps from bromobenzene. The key steps involved the enzymatic dihydroxylation, regioselective opening of epoxyaziridine 9 with the alane derived from 8, a solid-state silica-gel-catalyzed intramolecular opening of aziridine to produce phenanthrene 13 whose oxidative cleavage and recyclization provided the full skeleton of the Amaryllidaceae constituents. The new analogues 5 and 6 exhibited promising activity in several human cancer cell lines.