Formal synthesis of (-)-agelastatin A: An iron(II)-mediated cyclization strategy

Abstract

An iron(II)-mediated aminohalogenation of a cyclopentenyl N-tosyloxycarbamate provided new access to the key intermediate for the synthesis of (-)-agelastatin A (AA, 1), a potent antiproliferative alkaloid. The present synthetic endeavour offered an insight into the mechanism underlying the iron(II)-mediated aminohalogenation of N-tosyloxycarbamate, in which the radical properties of the N-iron intermediates in the redox states were operative. © 2013 Shigeoka et al; licensee Beilstein-Institut. Copyright 2013 BMJ Publishing Group. All rights reserved.