Synthesis of (+)-harmicine

TitleSynthesis of (+)-harmicine
Publication TypeJournal Article
Year of Publication2014
AuthorsMondal, P, Argade, NP
JournalSynthesis-Stuttgart
Volume46
Issue19
Pagination2591-2594
Date PublishedOCT
ISSN0039-7881
Keywordsalkaloids, 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.

DOI10.1055/s-0034-1378381
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.06
Divison category: 
Organic Chemistry