| Literature DB >> 21744783 |
Amanda C Cutter1, Iain R Miller, John F Keily, Richard K Bellingham, Mark E Light, Richard C D Brown.
Abstract
Short routes to enantiomerically pure indolizidine and quinolizidine alkaloids have been developed using imino-aldol reactions of enolates derived from phenyl 5-chlorovalerate. High levels of syn selectivity (dr ∼13-16:1) were obtained using lithium enolates of phenyl esters in combination with tert-butylsulfinyl imines. The imino-aldol adducts were deprotected and cyclized to afford (-)-epilupinine ((-)-2) and (-)-tashiromine ((-)-1) in two further steps.Entities:
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Year: 2011 PMID： 21744783 DOI： 10.1021/ol2015048
Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005