Synthesis of the core ring system of the stemona alkaloids by cascade condensation, cyclization, intramolecular cycloaddition.
Condensation of an aldehyde with an α-amino-ester, followed by a tandem process involving cyclization to a seven-membered ring, deprotonation to an intermediate azomethine ylide and intramolecular dipolar cycloaddition gave tricyclic products related to stenine and neostenine.
Burrell
Adam J M
AJ
Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, UKS3 7HF.
Watson
Luke
L
Martin
Nathaniel G
NG
Oram
Niall
N
Coldham
Iain
I
D000447:Aldehydes / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D003500:Cyclization; D041901:Stemonaceae / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000470:Alkaloids; D000588:Amines; C441784:stenine