Convergent and Scalable Synthesis of the ABCDE-Ring Fragment of Caribbean Ciguatoxin C-CTX-1

Makoto Sasaki; Miku Seida; Atsushi Umehara

doi:10.1021/acs.joc.2c02414

Convergent and Scalable Synthesis of the ABCDE-Ring Fragment of Caribbean Ciguatoxin C-CTX-1

Makoto Sasaki, Miku Seida, Atsushi Umehara

生命科学研究科・分子化学生物学専攻

研究成果: Article › 査読

抄録

Convergent and scalable synthesis of the ABCDE-ring fragment of Caribbean ciguatoxin C-CTX-1, the major causative toxin for ciguatera poisoning in the Caribbean Sea and the Northeast Atlantic areas, is described in detail. The key features of the synthesis include an iterative use of 2,2,6,6-tetramethyl piperidine 1-oxyl (TEMPO)/PhI(OAc)₂-mediated oxidative lactonization and Suzuki-Miyaura coupling en route to the DE-ring system and a convergent fragment coupling to form the ABCDE-ring skeleton via the Suzuki-Miyaura coupling strategy.

本文言語	English
ページ（範囲）	403-418
ページ数	16
ジャーナル	Journal of Organic Chemistry
巻	88
号	1
DOI	https://doi.org/10.1021/acs.joc.2c02414
出版ステータス	Published - 2023 1月 6

ASJC Scopus subject areas

有機化学

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10.1021/acs.joc.2c02414

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title = "Convergent and Scalable Synthesis of the ABCDE-Ring Fragment of Caribbean Ciguatoxin C-CTX-1",

abstract = "Convergent and scalable synthesis of the ABCDE-ring fragment of Caribbean ciguatoxin C-CTX-1, the major causative toxin for ciguatera poisoning in the Caribbean Sea and the Northeast Atlantic areas, is described in detail. The key features of the synthesis include an iterative use of 2,2,6,6-tetramethyl piperidine 1-oxyl (TEMPO)/PhI(OAc)2-mediated oxidative lactonization and Suzuki-Miyaura coupling en route to the DE-ring system and a convergent fragment coupling to form the ABCDE-ring skeleton via the Suzuki-Miyaura coupling strategy.",

author = "Makoto Sasaki and Miku Seida and Atsushi Umehara",

note = "Funding Information: This work was financially supported by JSPS KAKENHI grant no. JP20H02919. We are grateful to Dr. Masahiro Hirama (Emeritus Professor of Tohoku University) for his encouragement. We also thank Hiroto Takahashi (Tohoku University) for ESI-TOF/MS measurements, using a Bruker micrOTOF-Q II at Tagen Central Analytical Facility. Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

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AU - Umehara, Atsushi

N1 - Funding Information: This work was financially supported by JSPS KAKENHI grant no. JP20H02919. We are grateful to Dr. Masahiro Hirama (Emeritus Professor of Tohoku University) for his encouragement. We also thank Hiroto Takahashi (Tohoku University) for ESI-TOF/MS measurements, using a Bruker micrOTOF-Q II at Tagen Central Analytical Facility. Publisher Copyright: © 2022 American Chemical Society.

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Y1 - 2023/1/6

N2 - Convergent and scalable synthesis of the ABCDE-ring fragment of Caribbean ciguatoxin C-CTX-1, the major causative toxin for ciguatera poisoning in the Caribbean Sea and the Northeast Atlantic areas, is described in detail. The key features of the synthesis include an iterative use of 2,2,6,6-tetramethyl piperidine 1-oxyl (TEMPO)/PhI(OAc)2-mediated oxidative lactonization and Suzuki-Miyaura coupling en route to the DE-ring system and a convergent fragment coupling to form the ABCDE-ring skeleton via the Suzuki-Miyaura coupling strategy.

AB - Convergent and scalable synthesis of the ABCDE-ring fragment of Caribbean ciguatoxin C-CTX-1, the major causative toxin for ciguatera poisoning in the Caribbean Sea and the Northeast Atlantic areas, is described in detail. The key features of the synthesis include an iterative use of 2,2,6,6-tetramethyl piperidine 1-oxyl (TEMPO)/PhI(OAc)2-mediated oxidative lactonization and Suzuki-Miyaura coupling en route to the DE-ring system and a convergent fragment coupling to form the ABCDE-ring skeleton via the Suzuki-Miyaura coupling strategy.

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Convergent and Scalable Synthesis of the ABCDE-Ring Fragment of Caribbean Ciguatoxin C-CTX-1

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