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

✍ Scribed by Takumi Watanabe; Ikuko Kurata; Chigusa Hayashi; Masayuki Igarashi; Ryuichi Sawa; Yoshikazu Takahashi; Yuzuru Akamatsu

• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 346 KB
• Volume: 20
• Category: Article
• ISSN: 0960-894X
• DOI: 10.1016/j.bmcl.2010.07.115

✦ Synopsis

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.