Asymmetric synthesis of the quinolizidine alkaloid (-)-epimyrtine with intramolecular Mannich cyclization and N-sulfinyl delta-amino beta-ketoesters.
A concise, six-step, enantioselective synthesis of (-)-epimyrtine employing the N-sulfinyl delta-amino beta-ketoester chiral building block is described.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Zhang
Yulian
Y
Anilkumar
Gopinathan
G
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D015394:Molecular Structure; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013457:Sulfur Compounds / Q000737:chemistry*
D000470:Alkaloids; D004952:Esters; D011799:Quinazolines; D011807:Quinolizines; D013457:Sulfur Compounds; C482086:epimyrtine