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^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

28 Scopus citations

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.

Original language	English
Article number	ST-2013-U0890-L
Pages (from-to)	288-292
Number of pages	5
Journal	Synlett
Volume	25
Issue number	2
DOIs	https://doi.org/10.1055/s-0033-1340291
State	Published - 2014/01

Keywords

C-H insertion
C-H olefination
blechnic acids
chiral dirhodium(II) catalyst
dihydrobenzofuran neolignan

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0033-1340291

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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",

month = jan,

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

language = "英語",

volume = "25",

pages = "288--292",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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T1 - Asymmetric Total Synthesis of (-)- trans -Blechnic Acid via Rhodium(II)-Catalyzed C-H Insertion and Palladium(II)-Catalyzed C-H Olefination Reactions

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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U2 - 10.1055/s-0033-1340291

DO - 10.1055/s-0033-1340291

M3 - 学術論文

AN - SCOPUS:84892436243

SN - 0936-5214

VL - 25

SP - 288

EP - 292

JO - Synlett

JF - Synlett

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M1 - ST-2013-U0890-L

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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