Synthesis of 1-Azaspiro[4,5]-7-decen-2-one from L-Asparagine and L-Aspartic Acid

Abstract

A synthetic strategy for 1-azaspiro[4.5]-7-decen-2-one based on Nacyliminium spirocyclization is reported. The common core structure found in biologically active alkaloids such as FR901483, TAN1251 and lepadiformine was synthesized via chiral N-alkyl-3-dibenzylaminosuccinimide intermediates. The chiral succinimides were synthesized in 2 steps from L-aspartic acid or 3 steps from L-asparagine.