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.

Enantioselective formal synthesis of (-)-ovalicin using quinic acid as a chiral template

BARCO, Achille;BENETTI, Simonetta;DE RISI, Carmela;MARCHETTI, Paolo;POLLINI, Gian Piero;ZANIRATO, Vinicio
1998

Abstract

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.
1998
Barco, Achille; Benetti, Simonetta; DE RISI, Carmela; Marchetti, Paolo; Pollini, Gian Piero; Zanirato, Vinicio
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/1206937
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