A Palladium-Catalyzed Synthesis of Isoalliin, the Main Cysteine Sulfoxide in Onions (Allium cepa)

Abstract

The natural sulfur compound isoalliin, (+)-(R)-3-[(E)-prop-1-enylsulfinyl]-2-aminopropanoic acid, was synthesized as a mixture of diastereomers in five steps from the hydrochloride of l-cysteine ethyl ester comprising an efficient - albeit unusual - Pd-catalyzed C-S coupling as the key step. Isoalliin is in demand in the field of Allium chemistry and serves as a standard for different determination methods in breeding research on Alliaceae, like onions, leek, or garlic.

Key words

palladium - C-S coupling - natural product - amino acid - thiol

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