(-)-(S)-Nakinadine B: first asymmetric synthesis

(-)-(S)-Nakinadine B: first asymmetric synthesis

(-)-(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...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2012-09, Vol.48 (74), p.9236-9238
Hauptverfasser: Davies, Stephen G, Lee, James A, Roberts, Paul M, Shah, Rushabh S, Thomson, James E
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Asymmetry
Chemistry Techniques, Synthetic
Conjugates
Derivatives
Lithium
Models, Molecular
Molecular Conformation
Protonation
Pyridines - chemical synthesis
Pyridines - chemistry
Synthesis
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Zusammenfassung:(-)-(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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc34808j