Total Synthesis of Limonin

Shuji Yamashita, Akito Naruko, Yuki Nakazawa, Le Zhao, Yujiro Hayashi, Masahiro Hirama

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)8538-8541
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number29
DOIs
Publication statusPublished - 2015 Jul 13

Keywords

  • cycloaddition
  • limonoids
  • oxidation
  • radical reactions
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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