Synthesis of 3-azidopiperidine skeleton employing ceric ammonium nitrate (CAN)-mediated regioselective azidoalkoxylation of enol ether: total synthesis of d-2 receptor agonist (+/-)-quinagolide
| Title | Synthesis of 3-azidopiperidine skeleton employing ceric ammonium nitrate (CAN)-mediated regioselective azidoalkoxylation of enol ether: total synthesis of d-2 receptor agonist (+/-)-quinagolide |
| Publication Type | Journal Article |
| Year of Publication | 2018 |
| Authors | Chavan, SP, Kadam, AL, Lasonkar, PB, Gonnade, RG |
| Journal | Organic letters |
| Volume | 20 |
| Issue | 22 |
| Pagination | 7011-7014 |
| Date Published | NOV |
| Type of Article | Article |
| ISSN | 1523-7060 |
| Abstract | The total synthesis of (+/-)-quinagolide, which is a D-2 receptor agonist, was accomplished via a ceric ammonium nitrate (CAN)-mediated regioselective azidoalkoxylation of enol ether route. Key features of the synthesis include Claisen rearrangement, PPTS (pyridinium p-toluene-sulfonate)-catalyzed one-pot acetal deprotection, followed by a diastereoselective Henry reaction, which enables construction of the required trans ring junction and CAN-mediated regioselective azidoalkoxylation of enol ether. The PPTS-catalyzed intramolecular diastereoselective Henry reaction to fix three contiguous stereocenters on tetrahydronaphthalene and the first-of-its-kind synthesis of the 3-azidopiperidine skeleton, using a CAN -mediated regioselective azidoalkoxylation of enol ether, are important findings of the present work. |
| DOI | 10.1021/acs.orglett.8b02900 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.492 |
Divison category:
Organic Chemistry
Physical and Materials Chemistry
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