Stereoselective synthesis of 2,6-trans-4-oxopiperidines using an acid-mediated 6-endo-trig cyclisation.

doi:10.1039/c8ob01363b

Paper

Stereoselective synthesis of 2,6-trans-4-oxopiperidines using an acid-mediated 6-endo-trig cyclisation.

Published Sep 11, 2018 · J. D. Bell, Alexander H Harkiss, Christopher R. Wellaway

Organic & biomolecular chemistry

Q2 SJR score

4

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0

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Abstract

An acid-mediated 6-endo-trig cyclisation of amine-substituted enones has been developed for the stereoselective synthesis of trans-6-alkyl-2-methyl-4-oxopiperidines. Performed under conditions that prevent removal of the Boc-protecting group or acetal formation, the key cyclisation was found to generate cleanly the 4-oxopiperidine products in high overall yields from a wide range of alkyl substituted enones. The synthetic utility of the trans-6-alkyl-2-methyl-4-oxopiperidines formed from this process was demonstrated with the total synthesis of the quinolizidine alkaloid, (+)-myrtine and the piperidine alkaloid, (-)-solenopsin A.

Study Snapshot

Acid-mediated 6-endo-trig cyclisation effectively synthesizes stereoselective trans-6-alkyl-2-methyl-4-oxopiperidines in high yields, useful for the total synthesis of (+)-myrtine and (-)-solenopsin A.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Stereoselective synthesis of 2,6-trans-4-oxopiperidines using an acid-mediated 6-endo-trig cyclisation.

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