title: The first total synthesis of (-) and (+)-2-hydroxy-24-oxooctacosanolide using an effective lactonization.
abstract: [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.
authors.affiliation: Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. shiina@ch.kagu.tus.ac.jp
authors.forename: Isamu
authors.initials: I
authors.lastname: Shiina
authors.forename: Takaaki
authors.initials: T
authors.lastname: Kikuchi
authors.forename: Akane
authors.initials: A
authors.lastname: Sasaki
mesh_terms: D000818:Animals; D020049:Isoptera / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C520458:2-hydroxy-24-oxooctacosanolide; D007783:Lactones; D018942:Macrolides