title: Polysubstituted piperidines via iodolactonization: application to the asymmetric synthesis of (+)-pseudodistomin D.
abstract: Conjugate addition of lithium (S)-N-allyl-N-(α-methyl-p-methoxybenzyl)amide to methyl (E,E)-hepta-2,5-dienoate furnished the corresponding β-amino ester. N-Protecting group manipulation, ring-closing metathesis, and ester hydrolysis gave enantiopure [N(1')-tert-butoxycarbonyl-1,2,3,6-tetrahydropyridin-2'-yl]ethanoic acid. Subsequent iodolactonization gave a bicyclic iodolactone scaffold. This key intermediate was elaborated to (+)-pseudodistomin D [in >99% ee and 7% yield over 16 steps from methyl (E,E)-hepta-2,5-dienoate].
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. steve.davies@chem.ox.ac.uk
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Davies
authors.forename: Ai M
authors.initials: AM
authors.lastname: Fletcher
authors.forename: James A
authors.initials: JA
authors.lastname: Lee
authors.forename: Paul M
authors.initials: PM
authors.lastname: Roberts
authors.forename: Angela J
authors.initials: AJ
authors.lastname: Russell
authors.forename: Rachael J
authors.initials: RJ
authors.lastname: Taylor
authors.forename: Anthony D
authors.initials: AD
authors.lastname: Thomson
authors.forename: James E
authors.initials: JE
authors.lastname: Thomson
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D018360:Crystallography, X-Ray; D004952:Esters; D008968:Molecular Conformation; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014561:Urochordata / Q000737:chemistry
chemical_list: D000470:Alkaloids; D004952:Esters; D010880:Piperidines; C109385:pseudodistomin D