Arun K Ghosh1, Joshua R Born1, Luke A Kassekert1. 1. Department of Chemistry and Department of Medicinal Chemistry , Purdue University , 560 Oval Drive , West Lafayette , Indiana 47907 , United States.
Abstract
Enantioselective syntheses of hexacyclic aspidoalbidine alkaloids (+)-fendleridine (2) and (+)-acetylaspidoalbidine (3) are described. These syntheses feature an asymmetric decarboxylative allylation and photocyclization of a highly substituted enaminone. Also, the synthesis highlights the formation of a C19-hemiaminal ether via a reduction/condensation/intramolecular cyclization cascade with the C21-alcohol. The present synthesis provides convenient access to the aspidoalbidine hexacyclic alkaloid family in an efficient manner.
Enantioselective syntheses of hexacyclicn class="Chemical">aspidoalbidine alkaloids(+)-fendleridine (2) and (+)-acetylaspidoalbidine (3) are described. These syntheses feature an asymmetric decarboxylative allylation and photocyclization of a highly substituted enaminone. Also, the synthesis highlights the formation of a C19-hemiaminal ether via a reduction/condensation/intramolecular cyclization cascade with the C21-alcohol. The present synthesis provides convenient access to the aspidoalbidine hexacyclic alkaloid family in an efficient manner.
Authors: Gordon D Wilkie; Gregory I Elliott; Brian S J Blagg; Scott E Wolkenberg; Danielle R Soenen; Michael M Miller; Scott Pollack; Dale L Boger Journal: J Am Chem Soc Date: 2002-09-25 Impact factor: 15.419
Authors: J C A Tanaka; C C da Silva; A J B de Oliveira; C V Nakamura; B P Dias Filho Journal: Braz J Med Biol Res Date: 2006-02-22 Impact factor: 2.590