Formal synthesis of bioactive indole alkaloids eburnamonine, eburnaminol, and vindeburnol

TitleFormal synthesis of bioactive indole alkaloids eburnamonine, eburnaminol, and vindeburnol
Publication TypeJournal Article
Year of Publication2017
AuthorsMondal, P, Argade, NP
JournalSynthesis-Stuttgart
Volume49
Issue8
Pagination1849-1856
Date PublishedAPR
Type of ArticleArticle
ISSN0039-7881
Keywordscyclizations, eburnaminol, eburnamonine, elimination, hexahydroindoloquinolizinone, reduction, vindeburnol
Abstract

Starting from (+/-)-3-acetoxyglutarimide, diastereoselective formal synthesis of indole alkaloids (+/-)-eburnamonine, (+/-)-eburnaminol, and (+/-)-vindeburnol have been demonstrated via a common intermediate (+/-)-1-hydroxy-12-tosyl-2,3,6,7,12,12b-hexahydroindolo[2,3a] quinolizin-4(1H)-one in very good overall yields. The acetoxy group from (+/-)-3-acetoxyglutarimide was first used to induce the diastereoselectivity and also as a latent source of ketone carbonyl group. The stereoselective eliminations, reductions, and intramolecular cyclizations were the involved key steps.

DOI10.1055/s-0036-1588386
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.722
Divison category: 
Organic Chemistry

Add new comment