A concise asymmetric route to Nuphar alkaloids. A formal synthesis of (-)-deoxynupharidine.
[reaction: see text] A stereocontrolled route to Nuphar alkaloids is described that employs a formal [3 + 3] cycloaddition strategy to assemble the piperidine nucleus. The addition of Pd-TMM complexes to aziridine 10 was found to be sluggish; however, the addition of a functionalized allyl Grignard reagent followed by a Mitsunobu condensation reaction provided 11 in high yield. The employment of this route in the formal synthesis of (-)-deoxynupharidine 1 is described.
Moran
Wesley J
WJ
Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, U.K.
Goodenough
Katharine M
KM
Raubo
Piotr
P
Harrity
Joseph P A
JP
D000470:Alkaloids / Q000138:chemical synthesis*; D000498:Allyl Compounds / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry; D002384:Catalysis; D008956:Models, Chemical; D031654:Nuphar; D010165:Palladium / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis; D011807:Quinolizines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D000498:Allyl Compounds; D001388:Aziridines; D010880:Piperidines; D011807:Quinolizines; C010908:deoxynupharidine; D010165:Palladium