Formal synthesis of (-)-quinagolide: diastereoselective ring expansion via a bicyclic aziridinium ion strategy to access the octahydrobenzo[g]quinoline architecture
| Title | Formal synthesis of (-)-quinagolide: diastereoselective ring expansion via a bicyclic aziridinium ion strategy to access the octahydrobenzo[g]quinoline architecture |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Chavan, SP, Kawale, SA, Pisal, MM, Kadam, AL, Gonnade, RG |
| Journal | Journal of Organic Chemistry |
| Volume | 86 |
| Issue | 14 |
| Pagination | 9344-9352 |
| Date Published | JUL |
| Type of Article | Article |
| ISSN | 0022-3263 |
| Abstract | 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. |
| DOI | 10.1021/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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