The synthesis of paleic acid, an antimicrobial agent effective against Mannheimia and Pasteurella, and its structurally related derivatives.
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.
Watanabe
Takumi
T
Institute of Microbial Chemistry Tokyo 141-0021, Japan. twatanabe@bikaken.or.jp
Kurata
Ikuko
I
Hayashi
Chigusa
C
Igarashi
Masayuki
M
Sawa
Ryuichi
R
Takahashi
Yoshikazu
Y
Akamatsu
Yuzuru
Y
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
D000900:Anti-Bacterial Agents; D009829:Oleic Acids; C556099:paleic acid