Asymmetric Total Synthesis of (-)- trans -Blechnic Acid via Rhodium(II)-Catalyzed C-H Insertion and Palladium(II)-Catalyzed C-H Olefination Reactions

Motoki Ito; Ryosuke Namie; Janagiraman Krishnamurthi; Hitomi Miyamae; Koji Takeda; Hisanori Nambu; Shunichi Hashimoto

doi:10.1055/s-0033-1340291

Asymmetric Total Synthesis of (-)- trans -Blechnic Acid via Rhodium(II)-Catalyzed C-H Insertion and Palladium(II)-Catalyzed C-H Olefination Reactions

Motoki Ito, Ryosuke Namie, Janagiraman Krishnamurthi, Hitomi Miyamae, Koji Takeda, Hisanori Nambu, Shunichi Hashimoto^*

^*この論文の責任著者

分子合成化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

28 被引用数 (Scopus)

抄録

An asymmetric total synthesis of (-)-trans-blechnic acid, a dihydrobenzofuran neolignan, has been achieved. The key steps involve an elaboration of the cis-2,3-dihydrobenzofuran core structure by enantio- and diastereoselective intramolecular C-H insertion using dirhodium(II) tetrakis[N-phthaloyl-(R)-tert-leucinate] [Rh₂(R-PTTL)₄] and a direct coupling of an acrylate unit with the core structure employing Yu's palladium(II)-catalyzed intermolecular C-H olefination.

本文言語	英語
論文番号	ST-2013-U0890-L
ページ（範囲）	288-292
ページ数	5
ジャーナル	Synlett
巻	25
号	2
DOI	https://doi.org/10.1055/s-0033-1340291
出版ステータス	出版済み - 2014/01

ASJC Scopus 主題領域

有機化学

文献へのアクセス

10.1055/s-0033-1340291

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引用スタイル

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title = "Asymmetric Total Synthesis of (-)- trans -Blechnic Acid via Rhodium(II)-Catalyzed C-H Insertion and Palladium(II)-Catalyzed C-H Olefination Reactions",

abstract = "An asymmetric total synthesis of (-)-trans-blechnic acid, a dihydrobenzofuran neolignan, has been achieved. The key steps involve an elaboration of the cis-2,3-dihydrobenzofuran core structure by enantio- and diastereoselective intramolecular C-H insertion using dirhodium(II) tetrakis[N-phthaloyl-(R)-tert-leucinate] [Rh2(R-PTTL)4] and a direct coupling of an acrylate unit with the core structure employing Yu's palladium(II)-catalyzed intermolecular C-H olefination.",

keywords = "C-H insertion, C-H olefination, blechnic acids, chiral dirhodium(II) catalyst, dihydrobenzofuran neolignan",

author = "Motoki Ito and Ryosuke Namie and Janagiraman Krishnamurthi and Hitomi Miyamae and Koji Takeda and Hisanori Nambu and Shunichi Hashimoto",

year = "2014",

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doi = "10.1055/s-0033-1340291",

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AU - Ito, Motoki

AU - Namie, Ryosuke

AU - Krishnamurthi, Janagiraman

AU - Miyamae, Hitomi

AU - Takeda, Koji

AU - Nambu, Hisanori

AU - Hashimoto, Shunichi

PY - 2014/1

Y1 - 2014/1

N2 - An asymmetric total synthesis of (-)-trans-blechnic acid, a dihydrobenzofuran neolignan, has been achieved. The key steps involve an elaboration of the cis-2,3-dihydrobenzofuran core structure by enantio- and diastereoselective intramolecular C-H insertion using dirhodium(II) tetrakis[N-phthaloyl-(R)-tert-leucinate] [Rh2(R-PTTL)4] and a direct coupling of an acrylate unit with the core structure employing Yu's palladium(II)-catalyzed intermolecular C-H olefination.

AB - An asymmetric total synthesis of (-)-trans-blechnic acid, a dihydrobenzofuran neolignan, has been achieved. The key steps involve an elaboration of the cis-2,3-dihydrobenzofuran core structure by enantio- and diastereoselective intramolecular C-H insertion using dirhodium(II) tetrakis[N-phthaloyl-(R)-tert-leucinate] [Rh2(R-PTTL)4] and a direct coupling of an acrylate unit with the core structure employing Yu's palladium(II)-catalyzed intermolecular C-H olefination.

KW - C-H insertion

KW - C-H olefination

KW - blechnic acids

KW - chiral dirhodium(II) catalyst

KW - dihydrobenzofuran neolignan

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