The first active aza analogue of narciclasine was synthesized from a pentasubstituted derivative of nicotinic acid. The key features of the synthesis include a halogen dance of bromopyridine and an intramolecular Heck reaction with a conduramine derived chemoenzymatically from bromobenzene. 10-Aza-narciclasine was found to have reasonable activity against several cancer cell lines.

Synthesis and Biological Activity of 10-Aza-narciclasine. -Title compound (VI) is synthesized starting from pyridine derivative (I) over 12 steps in an overall yield of 2.05%. The key steps are the halogen dance reaction of (II) and the intramolecular Heck reaction of imide (IV). Compound (VI) is found to have reasonable activity against several cancer cell lines. -(VSHYVENKO, S.; W'GIORGIS, Z.; WEBER, A.; NEVEROVA, N.; HEDBERG, B.; HUDLICKY*, T.; Adv. Synth. Catal. 357 (2015) 1, 83-87, http://dx.doi.org/10.1002/adsc.201400993 ; Dep. Chem., Brock Univ., St. Catharines, Ont. L2S 3A1, Can.; Eng.) -R. Langenstrassen 22-246