The first total synthesis of (-) and (+)-2-hydroxy-24-oxooctacosanolide using an effective lactonization

Isamu Shiina; Takaaki Kikuchi; Akane Sasaki

doi:10.1021/ol062011o

The first total synthesis of (-) and (+)-2-hydroxy-24-oxooctacosanolide using an effective lactonization

Org Lett. 2006 Oct 12;8(21):4955-8. doi: 10.1021/ol062011o.

Authors

Isamu Shiina¹, Takaaki Kikuchi, Akane Sasaki

Affiliation

¹ Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. shiina@ch.kagu.tus.ac.jp

PMID: 17020345
DOI: 10.1021/ol062011o

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Isoptera / chemistry
Lactones / chemistry*
Macrolides / chemical synthesis*
Macrolides / chemistry
Molecular Structure
Stereoisomerism

Substances

2-hydroxy-24-oxooctacosanolide
Lactones
Macrolides