Synthesis of lactones using substituted benzoic anhydride as a coupling reagent.
This protocol describes a procedure for the synthesis of a 29-membered macrolactone. The facile mixed-anhydride method is very effective for the preparation of carboxylic esters and lactones using substituted benzoic anhydrides by the promotion of Lewis acid or basic catalysts under mild reaction conditions. Owing to the reaction rapidly proceeding to produce the monomeric compounds with high chemoselectivity, the protocol is quite powerful for the synthesis of not only the giant-sized lactones but also the highly strained cyclic compounds such as medium-sized lactones. The remarkable efficiency of the lactonizations promoted by the substituted benzoic anhydrides has been already shown in the synthesis of many natural complex molecules. It takes approximately 19 h to complete the protocol: 0.5 h to set up the reaction, 13.5 h for the reaction and 5 h for isolation and purification.
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
Fukui
Hiroki
H
Sasaki
Akane
A
D001565:Benzoates / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry
C525940:24-hydroxy-2-(4-methoxybenzyloxy)octacosanolide; D001565:Benzoates; D007783:Lactones; C102988:benzoic anhydride