Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid

Abstract

The naturally abundant, enantiomerically pure cyclitol quinic acid has been converted into a synthetically useful enone in nearly quantitative yield using the operationally straightforward and reproducible protocols reported herein. The latter compound, which was obtained in multigram quantities, engages in a diastereoselective 1,2-addition reaction with a hydrazone-based nucleophile. Furthermore, a readily derived α-iodoenone participates in both cross-coupling and α,β-annulation reactions. The results reported here emphasize that the now practically accessible cyclohexenones are useful, enantiomerically pure building blocks for organic synthesis.

Key Words

1,2-addition - α,β-annulation - cross-coupling - cyclohexenone - enantiomerically pure - α-iodination - quinic acid

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