Stereocontrolled Total Synthesis of (-)-Isocelorbicol and Its Elaboration to Natural Dihydro-β-agarofuran Esters

Tomoyo Mohri; Yusuke Takahashi; Eunsang Kwon; Shigefumi Kuwahara; Yusuke Ogura

doi:10.1021/acs.orglett.0c03419

Stereocontrolled Total Synthesis of (-)-Isocelorbicol and Its Elaboration to Natural Dihydro-β-agarofuran Esters

Tomoyo Mohri, Yusuke Takahashi, Eunsang Kwon, Shigefumi Kuwahara, Yusuke Ogura

研究成果: Article › 査読

3 被引用数 (Scopus)

抄録

The first total synthesis of four naturally occurring dihydro-β-agarofuran esters has been accomplished via a highly stereocontrolled 14-step access to their common core triol, (-)-isocelorbicol. A semipinacol rearrangement of an epoxy alcohol to install a quaternary carbon, diastereoselective conjugate reduction of a spirocyclic butenolide for the establishment of a methyl-bearing chiral center, and ring-closing metathesis to construct the decalin ring system were exploited as the key steps for the high-yielding synthesis of (-)-isocelorbicol.

本文言語	English
ページ（範囲）	9234-9238
ページ数	5
ジャーナル	Organic letters
巻	22
号	23
DOI	https://doi.org/10.1021/acs.orglett.0c03419
出版ステータス	Published - 2020 12月 4
外部発表	はい

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/acs.orglett.0c03419

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abstract = "The first total synthesis of four naturally occurring dihydro-β-agarofuran esters has been accomplished via a highly stereocontrolled 14-step access to their common core triol, (-)-isocelorbicol. A semipinacol rearrangement of an epoxy alcohol to install a quaternary carbon, diastereoselective conjugate reduction of a spirocyclic butenolide for the establishment of a methyl-bearing chiral center, and ring-closing metathesis to construct the decalin ring system were exploited as the key steps for the high-yielding synthesis of (-)-isocelorbicol. ",

author = "Tomoyo Mohri and Yusuke Takahashi and Eunsang Kwon and Shigefumi Kuwahara and Yusuke Ogura",

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AU - Mohri, Tomoyo

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AU - Kwon, Eunsang

AU - Kuwahara, Shigefumi

AU - Ogura, Yusuke

N1 - Funding Information: This work was financially supported by the Kato Memorial Bioscience Foundation. We thank Ms. Yuka Taguchi (Tohoku University) for her help with MS and NMR measurements. Publisher Copyright: © 2020 American Chemical Society

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Y1 - 2020/12/4

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AB - The first total synthesis of four naturally occurring dihydro-β-agarofuran esters has been accomplished via a highly stereocontrolled 14-step access to their common core triol, (-)-isocelorbicol. A semipinacol rearrangement of an epoxy alcohol to install a quaternary carbon, diastereoselective conjugate reduction of a spirocyclic butenolide for the establishment of a methyl-bearing chiral center, and ring-closing metathesis to construct the decalin ring system were exploited as the key steps for the high-yielding synthesis of (-)-isocelorbicol.

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Stereocontrolled Total Synthesis of (-)-Isocelorbicol and Its Elaboration to Natural Dihydro-β-agarofuran Esters

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