Synthesis of (+)-harmicine
| Title | Synthesis of (+)-harmicine |
| Publication Type | Journal Article |
| Year of Publication | 2014 |
| Authors | Mondal, P, Argade, NP |
| Journal | Synthesis-Stuttgart |
| Volume | 46 |
| Issue | 19 |
| Pagination | 2591-2594 |
| Date Published | OCT |
| ISSN | 0039-7881 |
| Keywords | alkaloids, cyclization, imides, reduction, stereoselective synthesis |
| Abstract | A facile convergent access to the important indole alkaloid (+)-harmicine is described, starting from tryptamine and (R)-acetoxysuccinic anhydride via the corresponding acetoxysuccinimide in very good overall yield. Regioselective reduction of an unsymmetrical imide carbonyl group and acid-catalyzed stereoselective intramolecular cyclization were the key features involved. The directing group to induce asymmetry was finally detached via the corresponding iodide by using tributyltin hydride chemistry. |
| DOI | 10.1055/s-0034-1378381 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.06 |
Divison category:
Organic Chemistry
