Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions

Amanda C Cutter; Iain R Miller; John F Keily; Richard K Bellingham; Mark E Light; Richard C D Brown

doi:10.1021/ol2015048

Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions

Org Lett. 2011 Aug 5;13(15):3988-91. doi: 10.1021/ol2015048. Epub 2011 Jul 11.

Authors

Amanda C Cutter¹, Iain R Miller, John F Keily, Richard K Bellingham, Mark E Light, Richard C D Brown

Affiliation

¹ The School of Chemistry, The University of Southampton, Highfield, Southampton SO17 1BJ, UK.

PMID: 21744783
DOI: 10.1021/ol2015048

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Cyclization
Imines / chemistry*
Indolizines / chemical synthesis*
Molecular Structure
Sparteine / analogs & derivatives*
Sparteine / chemical synthesis

Substances

Aldehydes
Imines
Indolizines
tashiromine
Sparteine
lupinine
3-hydroxybutanal