Total synthesis of avenaol

Motohiro Yasui, Rina Ota, Chihiro Tsukano () and Yoshiji Takemoto
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Motohiro Yasui: Kyoto University
Rina Ota: Kyoto University
Chihiro Tsukano: Kyoto University
Yoshiji Takemoto: Kyoto University

Nature Communications, 2017, vol. 8, issue 1, 1-9

Abstract: 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.

Date: 2017
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DOI: 10.1038/s41467-017-00792-1

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