Formal synthesis of (-)-quinagolide: diastereoselective ring expansion via a bicyclic aziridinium ion strategy to access the octahydrobenzo[g]quinoline architecture

TitleFormal synthesis of (-)-quinagolide: diastereoselective ring expansion via a bicyclic aziridinium ion strategy to access the octahydrobenzo[g]quinoline architecture
Publication TypeJournal Article
Year of Publication2021
AuthorsChavan, SP, Kawale, SA, Pisal, MM, Kadam, AL, Gonnade, RG
JournalJournal of Organic Chemistry
Volume86
Issue14
Pagination9344-9352
Date PublishedJUL
Type of ArticleArticle
ISSN0022-3263
AbstractThe 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.
DOI10.1021/acs.joc.1c00603
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)4.354
Divison category: 
Organic Chemistry
Physical and Materials Chemistry

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