Total synthesis of 2-hydroxytetracosanolide and 2-hydroxy-24-oxooctacosanolide by using an effective lactonization.
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).
Shiina
Isamu
I
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. shiina@rs.kagu.tus.ac.jp
Sasaki
Akane
A
Kikuchi
Takaaki
T
Fukui
Hiroki
H
D001565:Benzoates / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
C520458:2-hydroxy-24-oxooctacosanolide; C526945:2-hydroxytetracosanolide; D001565:Benzoates; D018942:Macrolides; D003300:Copper; C102988:benzoic anhydride