Concise total synthesis of (+/-)-aloperine and 6-epi-aloperine.
[reaction: see text] Total synthesis of aloperine and 6-epi-aloperine is reported. The crucial steps of the synthetic strategy are an aza-annulation reaction and an intermolecular Diels-Alder reaction. The synthetic plan proceeds from commercially available piperidine-2-ethanol.
Passarella
Daniele
D
Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Venezian 21, 20133 Milano, Italy. Daniele.Passarella@unimi.it
Angoli
Marco
M
Giardini
Alessandra
A
Lesma
Giordano
G
Silvani
Alessandra
A
Danieli
Bruno
B
D000470:Alkaloids / Q000138:chemical synthesis; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D054837:Quinolizidines; D013237:Stereoisomerism
D000470:Alkaloids; D010880:Piperidines; D054837:Quinolizidines; C062701:aloperine