Premium
Total Synthesis of Limonin
Author(s) -
Yamashita Shuji,
Naruko Akito,
Nakazawa Yuki,
Zhao Le,
Hayashi Yujiro,
Hirama Masahiro
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201503794
Subject(s) - limonin , limonoid , androstane , chemistry , stereochemistry , ring (chemistry) , total synthesis , radical cyclization , cycloaddition , singlet oxygen , tandem , terpene , organic chemistry , oxygen , catalysis , materials science , food science , composite material
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom