Stereoselective total synthesis of (-)-nupharamine utilizing an α-chlorosulfide and a sulfinimine for C-C bond formation.
An efficient stereoselective synthesis of the nuphar alkaloid, (-)-nupharamine, is reported. The key features include the Lewis acid catalyzed reaction of an α-chlorosulfide with a silyl ketene acetal for C-C bond formation, creation of the stereocenter at C2 by a diastereoselective reaction of allyl indium with a sulfinimine and reductive amination for the introduction of the C6 stereocenter of the piperidine ring.
Division of Natural Product Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India. sraghavan@iict.res.in.
Sadagopan
S
Raghavan
Sheelamanthula
S
Rajendar
D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013451:Sulfonic Acids / Q000737:chemistry*; D013452:Sulfonium Compounds / Q000737:chemistry*
D005663:Furans; D007097:Imines; D010880:Piperidines; D013451:Sulfonic Acids; D013452:Sulfonium Compounds; C520122:nupharamine; C522016:sulfinimine; C013880:chlorosulfonic acid