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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].

Original publication

DOI

10.1021/ol300209s

Type

Journal article

Journal

Org Lett

Publication Date

06/04/2012

Volume

14

Pages

1672 - 1675

Keywords

Alkaloids, Animals, Crystallography, X-Ray, Esters, Molecular Conformation, Molecular Structure, Piperidines, Stereoisomerism, Urochordata