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Total Syntheses of (−) Epilupinine and (−)-Tashiromine Using Imino-Aldol Reactions
- Source :
- Organic Letters. 13:3988-3991
- Publication Year :
- 2011
- Publisher :
- American Chemical Society (ACS), 2011.
-
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.
- 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
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 13
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....f8377266e54217af9b58f94f177a9c62