ChemInform Abstract: Chemoenzymatic Synthesis of (4S,5R)-5-Hydroxy-γ-decalactone.
Abstract
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ChemInform Abstract
Key step in the synthesis of the title hydroxy-γ-decalactone (VI) is the biochemical reduction of hydroxy ketone (I) to give a mixture of optically active dihydroxycarboxylic acids (II). Protection of the dihydroxyl moiety with isopropylidene group allows for the characterization and separation of the isomers (IV) and (V). trans-Isomer (IV) is transformed to the title lactone using acid reduction, Wittig olefination of the intermediary formed aldehyde, double bond reduction, and acid-mediated deprotection—lactonization.
