Concise and Environmentally Friendly Asymmetric Total Synthesis of the Putative Structure of a Biologically Active 3-Hydroxy-2-piperidone AlkaloidFinancial support was provided by CONACyT (project number: 255891) and the Marcos Moshinsky Foundation and BUAP-VIEP.
Received: 10 March 2018
Accepted after revision: 11 May 2018
26 June 2018 (online)
An asymmetric total synthesis of stereoisomers of a putative structure of 3-hydroxy-2-piperidone alkaloid derivative is described. This route is not only concise and efficient but also is achieved under an environmentally friendly approach. To this end, a direct and double C–H oxidation reaction of simple benzylated piperidine and Baker’s yeast reduction of a carbonyl group allowed the rapid access to the optically enriched (S)-1-benzyl-3-hydroxy-2-piperidone in only three steps. The NMR data agreed with those obtained in the first total synthesis (and in discrepancy with the natural product), however, optical rotation did not match with both neither the natural and synthetic material.
Key wordsalkaloids - 3-hydroxypiperidin-2-ones - total synthesis - environmentally friendly - TEMPO - C–H oxidation - sodium chlorite
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