Asymmetric total synthesis of (–)-rossinone A

[Display omitted] •The first total synthesis of (–)-rossinone A has been accomplished from geraniol in eight steps.•The key reactions include an asymmetric Davis oxidation and the HWE reaction.•Our approach would be applicable to the synthesis of other rossinone derivatives. The asymmetric total syn...

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Bibliographic Details
Published inTetrahedron letters Vol. 84; pp. 153456 - 153458
Main Authors Saito, Katsuya, Kurasawa, Kazuki, Takino, Chiaki, Kuwahara, Shigefumi, Enomoto, Masaru
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 09.11.2021
Elsevier
Subjects
Chemistry
Chemistry, Organic
Davis oxidation
Horner–Wadsworth–Emmons reaction
Meroterpene
Physical Sciences
Rossinone
Science & Technology
Horner–Wadsworth–Emmons reaction
Davis oxidation
Meroterpene
Rossinone
Horner-Wadsworth-Emmons reaction
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Summary:[Display omitted] •The first total synthesis of (–)-rossinone A has been accomplished from geraniol in eight steps.•The key reactions include an asymmetric Davis oxidation and the HWE reaction.•Our approach would be applicable to the synthesis of other rossinone derivatives. The asymmetric total synthesis of (–)-rossinone A, a meroterpene exhibiting a range of pharmacologically important biological activities, has been accomplished for the first time from geraniol by a concise eight-step sequence that involves the Horner–Wadsworth–Emmons reaction of an aldehyde derived from a geranylated hydroquinone intermediate with a chiral phosphonate prepared via the highly diastereoselective Davis oxidation of a known oxazolidinone derivative.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2021.153456