Methylpyridine Functionalization: Progress Towards the Synthesis of Lycopladine A and Monomorine

Abstract

A range of enones were found to participate in 1,4 conjugate addition with deprotonated 2-methylpyridines. Likewise, a transient 2,6 – lutidine anion was found to open 2-butyl-1-tosylaziridine at the less hindered end to form the addition product. An attempt was made to apply this 1,4 conjugate addition chemistry towards the synthesis of lycopladine A, a cytotoxic alkaloid. An attempt was also made to convert the aziridine opening product to monomorine, a 3,5 – indolizidine found in the Pharaoh worker ant Monomorium pharaonis.