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.

Keywords

• agelastatin
• aminohalogenation
• iron(II)
• free radical
• natural product synthesis