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Synthesis of Enantiomerically Pure (-)-Wine Lactone Based on a Palladium-Catalyzed Enantioselective Allylic Substitution (2000)

Bergner, Eike J. ; Helmchen, Günter

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 419-423

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Details

ISSN: 1434-193X

Schlagwort(e): Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: ---The first enantioselective synthesis of enantiomerically pure (-)-wine lactone, (-)-1a, a fragrance constituent of various white wines, and its epimer (+)-1b, was carried out. The key steps are allylic substitution of (±)-2-cyclohexen-1-yl acetate (2) with dimethylmalonate using palladium complexes of phosphanyldihydrooxazol L1 or of the phosphanylcarboxylic acid L2 as catalyst, subsequent decarboxylation, iodolactonization and elimination, furnishing enantiomerically pure bicyclic lactone (+)-7 in 47% overall yield. The diastereoselective introduction of methyl groups by SN2′-type substitution with an organocopper compound and by enolate alkylation gave lactone (-)-1a in 43% overall yield from (+)-7.

Materialart: Digitale Medien

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