title: Total synthesis of 2-hydroxytetracosanolide and 2-hydroxy-24-oxooctacosanolide by using an effective lactonization.
abstract: We have developed effective methods for the total synthesis of 2-hydroxytetracosanolide and 2-hydroxy-24-oxooctacosanolide, the defensive salivary secretions of termites. The former natural product isolated from Armitermes neotenicus, a species of termite that inhabits Guyana, contains a 25-membered lactone backbone, and the latter, extracted from Pseudacanthoterme springer, an African termite, includes a 29-membered lactone moiety. The key cyclization to produce the 25- or 29-membered lactone core is performed by using 2-methyl-6-nitrobenzoic anhydride (MNBA) with a stoichiometric amount of 4-(dimethylamino)pyridine (DMAP) or a catalytic amount of 4-(dimethylamino)pyridine N-oxide (DMAPO).
authors.affiliation: Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. shiina@rs.kagu.tus.ac.jp
authors.forename: Isamu
authors.initials: I
authors.lastname: Shiina
authors.forename: Akane
authors.initials: A
authors.lastname: Sasaki
authors.forename: Takaaki
authors.initials: T
authors.lastname: Kikuchi
authors.forename: Hiroki
authors.initials: H
authors.lastname: Fukui
mesh_terms: D001565:Benzoates / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: C520458:2-hydroxy-24-oxooctacosanolide; C526945:2-hydroxytetracosanolide; D001565:Benzoates; D018942:Macrolides; D003300:Copper; C102988:benzoic anhydride