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ID: ALA1255519

Journal: Bioorg Med Chem Lett

Title: The synthesis of paleic acid, an antimicrobial agent effective against Mannheimia and Pasteurella, and its structurally related derivatives.

Authors: Watanabe T, Kurata I, Hayashi C, Igarashi M, Sawa R, Takahashi Y, Akamatsu Y.

Abstract: A synthetic route to paleic acid 1, antimicrobial agent effective against Mannheimia haemolytica and Pasteurella multocida, has been established. The absolute configuration of the secondary hydroxyl group was controlled by a catalytic asymmetric alkylation of an aldehyde using a chiral titanium sulfonamide complex and the cis double bond was installed using a Wittig reaction. This synthetic route was also applied to the preparation of structurally related analogs, which were used in structure-activity relationship studies for antibacterial activity.

CiteXplore: 20728353

DOI: 10.1016/j.bmcl.2010.07.115