Total Synthesis of Limonin1. (3rd June 2015)

• Record Type: Journal Article
• Authors: Yamashita, Shuji; Naruko, Akito; Nakazawa, Yuki; Zhao, Le; Hayashi, Yujiro; Hirama, Masahiro
• Is Part Of: Angewandte Chemie. Volume 127:Number 29(2015)
• Page Start: 8658
• Page End: 8661
• Publication Date: 2015-06-03
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201503794
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Limonoids are highly oxygenated C13α‐triterpenes and common secondary metabolites. Several hundred congeners have been isolated to date. The first total synthesis of (±)‐limonin, the flagship congener of the limonoids, is now reported and features 1) a tandem radical cyclization generating the BCD ring system with the C13α configuration that is essential to the limonoids and a Robinson annulation to construct the limonoid androstane framework, 2) a singlet‐oxygen cycloaddition and a Baeyer–Villiger oxidation to synthesize the highly oxidized D ring, and 3) a Suárez reaction to construct the unique AA′ ring system.</p> </abstract>