Search

Your search keyword '"Iain R. Miller"' showing total 2 results
Start Over Author "Iain R. Miller"
2 results on '"Iain R. Miller"'

2. Total Syntheses of (−) Epilupinine and (−)-Tashiromine Using Imino-Aldol Reactions

Author

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

Subjects
Aldehydes, Quinolizidine, Molecular Structure, Chemistry, Sparteine, Organic Chemistry, Indolizines, chemistry.chemical_element, Indolizidine, Biochemistry, Adduct, chemistry.chemical_compound, Aldol reaction, Cyclization, Epilupinine, Organic chemistry, Lithium, Imines, Physical and Theoretical Chemistry, Selectivity, Tashiromine
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.

Published
2011

Catalog

Books, media, physical & digital resources
See catalog results