Total Syntheses of (+)-Aquatolide and Related Humulanolides

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

doi:10.1002/anie.201904404

Total Syntheses of (+)-Aquatolide and Related Humulanolides

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

Department of Applied Chemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	9851-9855
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	29
DOIs	https://doi.org/10.1002/anie.201904404
Publication status	Published - 2019 Jul 15

Keywords

biomimetic synthesis
cycloaddition
metathesis
terpenoids
total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201904404

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Takao, K. I., Kai, H., Yamada, A., Fukushima, Y., Komatsu, D., Ogura, A., & Yoshida, K. (2019). Total Syntheses of (+)-Aquatolide and Related Humulanolides. Angewandte Chemie - International Edition, 58(29), 9851-9855. https://doi.org/10.1002/anie.201904404

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