ChemInform Abstract: Synthetic and DFT Studies Towards a Unified Approach to Phlegmarine Alkaloids: Aza‐Michael Intramolecular Processes Leading to 5‐Oxodecahydroquinolines.

Abstract

Synthetic and DFT Studies Towards a Unified Approach to Phlegmarine Alkaloids: Aza-Michael Intramolecular Processes Leading to 5-Oxodecahydroquinolines. -(BRADSHAW*, B.; LUQUE-CORREDERA, C.; SABORIT, G.; CATIVIELA, C.; DOREL, R.; BO, C.; BONJOCH, J.; Chem. -Eur.

Access to Enantiopure 5-, 7-, and 5,7-Substituted cis-Decahydroquinolines: Enantioselective Synthesis of (−)-Cermizine B

“…We report herein the use of a new phenylglycinol-derived tricyclic lactam 3 as the key building block for the enantioselective synthesis of cermizine B, a member of the small group of phlegmarine-type Lycopodium alkaloids, which are characterized by a DHQ ring bearing a C-7 methyl substituent and a C-5 2-piperidylmethyl-based side chain (Figure ). We also report a joint experimental–computational study carried out to understand the factors governing the stereoselectivity of the cyclocondensation reactions leading to 3 and related tricyclic lactams.…”