DYKAT of vinyl aziridines: total synthesis of (+)-pseudodistomin D.
A concise total synthesis of (+)-pseudodistomin D was developed. The absolute stereochemistry was established through a dynamic kinetic asymmetric cycloaddition of an isocyanate to a vinyl aziridine. The piperidine core was constructed through a silver(I)-catalyzed hydroamination of an alkyne and subsequent diastereo- and regioselective reduction. [reaction: see text]
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA. bmtrost@stanford.edu
Fandrick
Daniel R
DR
D000470:Alkaloids / Q000138:chemical synthesis*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D007700:Kinetics; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D000470:Alkaloids; D001388:Aziridines; D010880:Piperidines; D014753:Vinyl Compounds; C109385:pseudodistomin D