Asymmetric total synthesis of (–)-rossinone A

Katsuya Saito; Kazuki Kurasawa; Chiaki Takino; Shigefumi Kuwahara; Masaru Enomoto

doi:10.1016/j.tetlet.2021.153456

Asymmetric total synthesis of (–)-rossinone A

Katsuya Saito, Kazuki Kurasawa, Chiaki Takino, Shigefumi Kuwahara, Masaru Enomoto

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Article number	153456
Journal	Tetrahedron Letters
Volume	84
DOIs	https://doi.org/10.1016/j.tetlet.2021.153456
Publication status	Published - 2021 Nov 9

Keywords

Davis oxidation
Horner–Wadsworth–Emmons reaction
Meroterpene
Rossinone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2021.153456

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title = "Asymmetric total synthesis of (–)-rossinone A",

abstract = "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.",

keywords = "Davis oxidation, Horner–Wadsworth–Emmons reaction, Meroterpene, Rossinone",

author = "Katsuya Saito and Kazuki Kurasawa and Chiaki Takino and Shigefumi Kuwahara and Masaru Enomoto",

note = "Funding Information: We are grateful to Ms. Taguchi (Tohoku University) for her help with NMR and MS measurements. This work was financially supported by JSPS KAKENHI (Grant No. 19K05837), JSPS Core-to-Core Program (Advanced Research Networks) entitled “Establishment of international agricultural immunology research-core for a quantum improvement in food safety,” and AMED (Grant No. JP19am0101100). Publisher Copyright: {\textcopyright} 2021 Elsevier Ltd",

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AU - Saito, Katsuya

AU - Kurasawa, Kazuki

AU - Takino, Chiaki

AU - Kuwahara, Shigefumi

AU - Enomoto, Masaru

N1 - Funding Information: We are grateful to Ms. Taguchi (Tohoku University) for her help with NMR and MS measurements. This work was financially supported by JSPS KAKENHI (Grant No. 19K05837), JSPS Core-to-Core Program (Advanced Research Networks) entitled “Establishment of international agricultural immunology research-core for a quantum improvement in food safety,” and AMED (Grant No. JP19am0101100). Publisher Copyright: © 2021 Elsevier Ltd

PY - 2021/11/9

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N2 - 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.

AB - 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.

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KW - Rossinone

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Asymmetric total synthesis of (–)-rossinone A

Abstract

Keywords

ASJC Scopus subject areas

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