Bioorganic & Medicinal Chemistry Letters 2011-08-15

Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation.

Sergey Vshyvenko, Jon Scattolon, Tomas Hudlicky, Anntherese E Romero, Alexander Kornienko

Index: Bioorg. Med. Chem. Lett. 21(16) , 4750-2, (2011)

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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.Copyright © 2011 Elsevier Ltd. All rights reserved.