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(-)-(S)-Nakinadine B has been synthesized for the first time (in 9 steps and 17% overall yield from commercially available atropic acid) using the conjugate addition of lithium dibenzyl-amide to an N-α-phenylacryloyl SuperQuat derivative with in situ diastereoselective enolate protonation as the key step.

Original publication

DOI

10.1039/c2cc34808j

Type

Journal article

Journal

Chem Commun (Camb)

Publication Date

25/09/2012

Volume

48

Pages

9236 - 9238

Keywords

Alkaloids, Chemistry Techniques, Synthetic, Models, Molecular, Molecular Conformation, Pyridines