2017年9月
Total synthesis of avenaol
NATURE COMMUNICATIONS
- ,
- ,
- ,
- 巻
- 8
- 号
- 1
- 開始ページ
- 674
- 終了ページ
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1038/s41467-017-00792-1
- 出版者・発行元
- NATURE PUBLISHING GROUP
Avenaol, isolated from the allelopathic plant black oat, was the first C-20 germination stimulant related to strigolactones. Structurally, it consisted of a bicyclo[4.1.0] heptanone skeleton containing a cyclopropane ring bearing three main chains projecting in the same direction (i.e. all-cis-substituted cyclopropane). Herein, we report the total synthesis of avenaol using a robust strategy involving the formation of an all-cis-substituted cyclopropane via an alkylidenecyclopropane. The key factors in the success of this total synthesis include the Rh-catalysed intramolecular cyclopropanation of an allene, an Ir-catalysed stereoselective double-bond isomerisation, and the differentiation of two hydroxymethyl groups via the regioselective formation and oxidation of a tetrahydropyran based on the reactivity of a cyclopropyl group. This strategy effectively avoids the undesired ring opening of the cyclopropane ring and the formation of a caged structure. Furthermore, this study confirms the proposed structure of avenaol, including its unique all-cis-substituted cyclopropane moiety.
- リンク情報
- ID情報
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- DOI : 10.1038/s41467-017-00792-1
- ISSN : 2041-1723
- ORCIDのPut Code : 36915405
- PubMed ID : 28939863
- Web of Science ID : WOS:000411526700019