A concise and convergent route to 5,8-disubstituted indolizidine and 1,4-disubstituted quinolizidine ring cores by diastereoselective aza-Diels-Alder reaction.
[reaction: see text] A short and convergent synthesis of 5,8-disubstituted indolizidine and 1,4-quinolizidine scaffolds is described. The key steps of the synthetic pathway are the aza-Diels-Alder reaction of a 2-aminodiene with an N-allyl or N-homoallylaldimine and a ring-closing metathesis. The bicyclic alkaloid analogues are obtained with total diastereoselectivity and through a common pathway.
Barluenga
José
J
Instituto Universitario de Química Organometálica Enrique Moles, Unidad asociada al C.S.I.C., Universidad de Oviedo, 33071 Oviedo, Spain. barluenga@sauron.quimica.uniovi.es
Mateos
Carlos
C
Aznar
Fernando
F
Valdés
Carlos
C
D000470:Alkaloids / Q000138:chemical synthesis*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis; D007202:Indicators and Reagents; D007212:Indolizines / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D011807:Quinolizines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D001643:Bridged Bicyclo Compounds; D007202:Indicators and Reagents; D007212:Indolizines; D011807:Quinolizines