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Total synthesis of avenaol

Author

Listed:
  • Motohiro Yasui

    (Kyoto University)

  • Rina Ota

    (Kyoto University)

  • Chihiro Tsukano

    (Kyoto University)

  • Yoshiji Takemoto

    (Kyoto University)

Abstract

Avenaol, isolated from the allelopathic plant black oat, was the first C20 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.

Suggested Citation

  • Motohiro Yasui & Rina Ota & Chihiro Tsukano & Yoshiji Takemoto, 2017. "Total synthesis of avenaol," Nature Communications, Nature, vol. 8(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_s41467-017-00792-1
    DOI: 10.1038/s41467-017-00792-1
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