title: The synthesis of paleic acid, an antimicrobial agent effective against Mannheimia and Pasteurella, and its structurally related derivatives.
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.
authors: Institute of Microbial Chemistry Tokyo 141-0021, Japan. twatanabe@bikaken.or.jp
authors: Takumi
authors: T
authors: Watanabe
authors: Ikuko
authors: I
authors: Kurata
authors: Chigusa
authors: C
authors: Hayashi
authors: Masayuki
authors: M
authors: Igarashi
authors: Ryuichi
authors: R
authors: Sawa
authors: Yoshikazu
authors: Y
authors: Takahashi
authors: Yuzuru
authors: Y
authors: Akamatsu
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D016978:Mannheimia haemolytica / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D009829:Oleic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D016979:Pasteurella multocida / Q000187:drug effects*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D009829:Oleic Acids; C556099:paleic acid