Total Syntheses of (+)-Aquatolide and Related Humulanolides

Ken ichi Takao, Hirotaka Kai, Ai Yamada, Yuuki Fukushima, Daisuke Komatsu, Akihiro Ogura, Keisuke Yoshida

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The short, efficient total synthesis of (+)-aquatolide was achieved by a biomimetic transannular [2+2] photocycloaddition, and provides the first example of constructing a 5/5/4/8-ring system from asteriscunolides. Furthermore, the reaction leading to a 5/4/4/7-ring system, the originally proposed structure of aquatolide, was also developed. This strategy achieved syntheses of five more humulanolides, (−)-asteriscunolides A, C, D, and I, and (+)-tetradehydroasteriscanolide.

Original languageEnglish
Pages (from-to)9851-9855
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number29
DOIs
Publication statusPublished - 2019 Jul 15

Keywords

  • biomimetic synthesis
  • cycloaddition
  • metathesis
  • terpenoids
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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