Ether-directed, stereoselective aza-Claisen rearrangements: synthesis of the piperidine alkaloid, alpha-conhydrine.
[reaction: see text] A new approach for the stereoselective synthesis of the piperidine alkaloid (+)-alpha-conhydrine and its pyrrolidine derivative has been developed using a palladium(II)-catalyzed, MOM-ether-directed aza-Claisen rearrangement and ring-closing metathesis to effect the key steps.
Jamieson
Andrew G
AG
WestCHEM, Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK.
Sutherland
Andrew
A
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D004986:Ether / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D001372:Aza Compounds; D010880:Piperidines; D020005:Propanols; D011759:Pyrrolidines; C520251:alpha-conhydrine; D004986:Ether; C006463:allyl alcohol; C032727:piperidine; C032519:pyrrolidine