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Enantio and diastereoselective total synthesis of all four stereoisomers of germicidin N

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Abstract Germicidin N (3-ethyl-4-hydroxy-6-[(1S, 2 R)−2-hydroxy-1-methylpropyl]-2H-pyran-2-one, 1), a new α-pyrone from the extracts of a Streptomyces sp. derived from marine algae, has been synthesized for the first time as four possible… Click to show full abstract

Abstract Germicidin N (3-ethyl-4-hydroxy-6-[(1S, 2 R)−2-hydroxy-1-methylpropyl]-2H-pyran-2-one, 1), a new α-pyrone from the extracts of a Streptomyces sp. derived from marine algae, has been synthesized for the first time as four possible diastereomers from chiral β-hydroxyester ((S)−6 and (R)−9) through the stereoselective alkylation, Claisen condensation followed by cyclization in a straightforward manner. Graphical Abstract

Keywords: enantio diastereoselective; synthesis four; diastereoselective total; total synthesis; four stereoisomers; stereoisomers germicidin

Journal Title: Synthetic Communications
Year Published: 2020

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