Total Syntheses of (+)-Aquatolide and Related Humulanolides

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

Research output: Contribution to journal › Article

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
JournalAngewandte Chemie - International Edition
DOIs
Publication statusPublished - 2019 Jan 1

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Biomimetics
aquatolide

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Total Syntheses of (+)-Aquatolide and Related Humulanolides. / Takao, Kenichi; Kai, Hirotaka; Yamada, Ai; Fukushima, Yuuki; Komatsu, Daisuke; Ogura, Akihiro; Yoshida, Keisuke.

In: Angewandte Chemie - International Edition, 01.01.2019.

Research output: Contribution to journal › Article

Takao, K, Kai, H, Yamada, A, Fukushima, Y, Komatsu, D, Ogura, A & Yoshida, K 2019, 'Total Syntheses of (+)-Aquatolide and Related Humulanolides', Angewandte Chemie - International Edition. https://doi.org/10.1002/anie.201904404
Takao K, Kai H, Yamada A, Fukushima Y, Komatsu D, Ogura A et al. Total Syntheses of (+)-Aquatolide and Related Humulanolides. Angewandte Chemie - International Edition. 2019 Jan 1. https://doi.org/10.1002/anie.201904404
Takao, Kenichi ; Kai, Hirotaka ; Yamada, Ai ; Fukushima, Yuuki ; Komatsu, Daisuke ; Ogura, Akihiro ; Yoshida, Keisuke. / Total Syntheses of (+)-Aquatolide and Related Humulanolides. In: Angewandte Chemie - International Edition. 2019.
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