Enantioselective formal synthesis of (−)-ovalicin (cas 19683-98-8) using quinic acid as a chiral template1

Add time:09/08/2019    Source:sciencedirect.com

The key intermediate 18 for the synthesis of (−)-ovalicin was synthesized using (−)-quinic acid as the chiral source, through a series of stereocontrolled and efficient chemical reactions, thus establishing a new, formal synthesis of the natural target. The featuring spirocyclic epoxide function has been installed by internal Williamson ether synthesis using the functionalities originally present at C-1 of (−)-quinic acid after the appropriate adjustments required to introduce the necessary functionality at C-2.

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