Synthesis of (±)-Serralongamine A and the Revised Structure of Huperzine N

• DOI: 10.1021/acs.joc.6b00025
• Publication Date: 2016-03-01T16:09:13Z
• Authors: Gisela V. Saborit; Caroline Bosch; Teodor Parella; Ben Bradshaw; Josep Bonjoch
• Keywords: Huperzine A

A revised structure for the Lycopodium alkaloid huperzine N is proposed and confirmed by synthesis. The key synthetic steps involve an epimerization of a cis-5-oxodecahydroquinoline to corresponding trans isomer coupling, followed diastereoselective hydrogenation using Wilkinson's catalyst incorporate pyridylmethyl moiety. This route allowed serralongamine be synthesized first time, two additional led N, both products bearing unusual decahydroquinoline stereostructure.