%0 Journal Article %J Journal of Organic Chemistry %D 2021 %T Formal synthesis of (-)-quinagolide: diastereoselective ring expansion via a bicyclic aziridinium ion strategy to access the octahydrobenzo[g]quinoline architecture %A Chavan, Subhash P. %A Kawale, Sanket A. %A Pisal, Mahesh M. %A Kadam, Appasaheb L. %A Gonnade, Rajesh G. %X The diastereoselective formal synthesis of (-)-quinagolide, a D-2 receptor agonist, has been achieved. The synthesis started from L-pyroglutamic acid and relied on utilization of (a) a stereospecific catalytic hydrogenation and diastereoselective Horner-Emmons-Michael cascade to obtain functionalized prolinate, (b) a Lewis acid mediated Pummerer cyclization to construct a tricyclic fused ring system, and (c) a diastereoselective ring expansion via a bicyclic aziridinium intermediate to access the required 3-substituted piperidine scaffold. %B Journal of Organic Chemistry %V 86 %P 9344-9352 %8 JUL %G eng %N 14 %9 Article %3 Foreign %4 4.354 %R 10.1021/acs.joc.1c00603