Total synthesis of (+)-trans- dihydronarciclasine from (+)-7-azabicyclo[2.2.1]heptanone
| Title | Total synthesis of (+)-trans- dihydronarciclasine from (+)-7-azabicyclo[2.2.1]heptanone |
| Publication Type | Journal Article |
| Year of Publication | 2018 |
| Authors | Pandey, G, Fernandes, R, Dey, D, Majumder, B |
| Journal | Tetrahedron |
| Volume | 74 |
| Issue | 39 |
| Pagination | 5752-5757 |
| Date Published | SEP |
| Type of Article | Article |
| Abstract | A concise asymmetric total synthesis of Amaryllidaceae alkaloid (+)-trans-dihydronarciclasine is accomplished starting from optically pure 7-azabicyclo[2.2.1]heptanone scaffold in 13 linear steps. Key features of the strategy include substrate-directed stereoselective installation of the trans B-C ring junction and regioselective Wacker-type internal olefin oxidation to provide a rapid access to all hydroxyl functionalities over the key cyclohexane ring in a stereocontrolled manner. (C) 2018 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tet.2018.08.016 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.377 |
Divison category:
Organic Chemistry