Straightforward Enantioselective Synthesis of Both Enantiomers of Karahana Lactone Using a Domino Ring-Closure Sequence

Jean-Marie Galano; Gérard Audran; Honoré Monti

doi:10.1016/S0040-4020(00)00645-1

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Straightforward Enantioselective Synthesis of Both Enantiomers of Karahana Lactone Using a Domino Ring-Closure Sequence

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Straightforward Enantioselective Synthesis of Both Enantiomers of Karahana Lactone Using a Domino Ring-Closure Sequence

Jean-Marie Galano, Gérard Audran et Honoré Monti

Tetrahedron, Vol.56(38), pp.7477-7481

15/09/2000

DOI: https://doi.org/10.1016/S0040-4020(00)00645-1

Résumé

(+)/(−)-karahana ether

(+)/(−)-karahana lactone

domino reaction

lipase

A straightforward enantioselective synthesis of both enantiomers of karahana lactone is described starting from enantiopure ( R) or ( S)-4-hydroxy-3-methyl-cyclohex-2-en-1-one. The key step of the sequence is an acid-induced domino reaction with three pathways running. Because of the first description of karahana lactone as a solid, the structure was secured by X-ray structural analysis.

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Titre: Straightforward Enantioselective Synthesis of Both Enantiomers of Karahana Lactone Using a Domino Ring-Closure Sequence
Créateurs - sans rôle: Jean-Marie Galano
Gérard Audran
Honoré Monti
Détails de publication: Tetrahedron, Vol.56(38), pp.7477-7481
Éditeur: Elsevier Ltd
Nombre de pages: 5
Identifiants: 99138727209311
Unité académique: Institut des Biomolécules Max Mousseron - IBMM
Langue: English
Type de ressource: Journal article