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.
