Synthesis of Potent CERT Inhibitor HPA-12 Featuring a Tandem Corey–Link and Intramolecular Nucleophilic Acyl Substitution Reaction

Dedicated to Prof. Scott E. Denmark on the occasion of his 60^th birthday

Abstract

A novel preparation of the potent CERT protein inhibitor (1R,3S)-HPA-12 is described. The synthesis is accomplished in five steps from (S)-Wynberg lactone and features a diastereoselective tandem Corey–Link and intramolecular nucleophilic acyl substitution reaction in a key step.

Key words

HPA-12 - CERT protein - gem-dichloroepoxide - Corey­–Link reaction - Wynberg lactone

• References

• 1 Address: Department of Chemistry and Physics, Southeastern Louisiana University, SLU 10878 Hammond, LA 70402, USA.
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