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