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

Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.
Chemical Communications (Impact Factor: 6.83). 08/2012; 48(74):9236-8. DOI: 10.1039/c2cc34808j
Source: PubMed


(-)-(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.

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