The first total synthesis of (-) and (+)-2-hydroxy-24-oxooctacosanolide using an effective lactonization.
[structure: see text] An effective method for the total synthesis of 2-hydroxy-24-oxooctacosanolide, a defensive salivary secretion of the African termite Pseudacanthotermes spiniger, has been developed. The key lactonization to form a 29-membered ring lactone core is performed using 2-methyl-6-nitrobenzoic anhydride with a catalytic amount of 4-(dimethylamino)pyridine N-oxide.
Shiina
Isamu
I
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. shiina@ch.kagu.tus.ac.jp
Kikuchi
Takaaki
T
Sasaki
Akane
A
D000818:Animals; D020049:Isoptera / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
C520458:2-hydroxy-24-oxooctacosanolide; D007783:Lactones; D018942:Macrolides