Asymmetric synthesis of functionalized trans-2,6-disubstituted piperidines with N-sulfinyl delta-amino beta-ketoesters. Synthesis of (-)-lasubine I.
[reaction: see text] The hydroxy-directed reduction of 1,2-dehydropiperidines with the "ate" complex of DIBAL-H and n-BuLi affords functionalized trans-2,6-disubstituted piperidines. This methodology was employed in the asymmetric synthesis of the quinolizidine alkaloid (-)-lasubine I.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Rao
Ashwin
A
Carroll
Patrick J
PJ
D004952:Esters / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry
D004952:Esters; D007659:Ketones; D010880:Piperidines; D011807:Quinolizines; D013457:Sulfur Compounds; C414385:lasubin I