Total synthesis of murraol, (E)-Suberenol and toward the collective total synthesis of exotines A, cnidimonins A-Cetc

Simple and efficient syntheses of murraol and (E)-suberenol were accomplished in just three simple steps from cheap and readily available 4-methoxysalicylaldehyde implementing a protecting-group-free and redox-neutral strategy. In the adopted approach, a practical regioselective bromination reaction...

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Veröffentlicht in:Tetrahedron 2022-11, Vol.126, p.133061, Article 133061
Hauptverfasser: Gong, Xushun, Bai, Mengjiao, Lu, Guidong, Yang, Binquan, Lei, Ting, Jiang, Shizhi
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Sprache:eng
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Zusammenfassung:Simple and efficient syntheses of murraol and (E)-suberenol were accomplished in just three simple steps from cheap and readily available 4-methoxysalicylaldehyde implementing a protecting-group-free and redox-neutral strategy. In the adopted approach, a practical regioselective bromination reaction and a high yield Mizoroki-Heck reaction from previously inactive bromocoumarin were conducted. This newly established high yield, gram scale synthetic method was further furnished the formal synthesis of a series of novel dimeric natural products. [Display omitted] •A simple and efficient total synthesis of Murraol and (E)-Suberenol were achieved, or one step from the known starting material in almost quantitative yield.•A protecting-group-free and redox-neutral strategy has been used.•These synthetic strategies and methodologies are further utilized in the formal synthesis of a series of novel dimeric natural products.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2022.133061