Convergent Synthesis of the HIJKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1 by a Late-Stage Reductive Olefin Coupling Approach

Makoto Sasaki; Kotaro Iwasaki; Keisuke Arai; Naoya Hamada; Atsushi Umehara

doi:10.1246/bcsj.20220070

Convergent Synthesis of the HIJKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1 by a Late-Stage Reductive Olefin Coupling Approach

Makoto Sasaki, Kotaro Iwasaki, Keisuke Arai, Naoya Hamada, Atsushi Umehara

LIF - Molecular and Chemical Life Science

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

1 Citation (Scopus)

Abstract

The convergent synthesis of the HIJKLMN-ring fragment of Caribbean ciguatoxin C-CTX-1, the major causative toxin for ciguatera fish poisoning in the Caribbean Sea and the Northeast Atlantic areas, is disclosed. The synthesis features a late-stage iron-catalyzed hydrogen atom transfer-initiated reductive olefin coupling to install the N-ring and a SuzukiMiyaura coupling/ thioacetalization strategy for the convergent assembly of the hexacyclic HIJKLM-ring skeleton.

Original language	English
Pages (from-to)	819-824
Number of pages	6
Journal	Bulletin of the Chemical Society of Japan
Volume	95
Issue number	5
DOIs	https://doi.org/10.1246/bcsj.20220070
Publication status	Published - 2022 May

Keywords

Caribbean ciguatoxin
Convergent synthesis
Cross coupling

ASJC Scopus subject areas

Chemistry(all)

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10.1246/bcsj.20220070

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title = "Convergent Synthesis of the HIJKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1 by a Late-Stage Reductive Olefin Coupling Approach",

abstract = "The convergent synthesis of the HIJKLMN-ring fragment of Caribbean ciguatoxin C-CTX-1, the major causative toxin for ciguatera fish poisoning in the Caribbean Sea and the Northeast Atlantic areas, is disclosed. The synthesis features a late-stage iron-catalyzed hydrogen atom transfer-initiated reductive olefin coupling to install the N-ring and a SuzukiMiyaura coupling/ thioacetalization strategy for the convergent assembly of the hexacyclic HIJKLM-ring skeleton.",

keywords = "Caribbean ciguatoxin, Convergent synthesis, Cross coupling",

author = "Makoto Sasaki and Kotaro Iwasaki and Keisuke Arai and Naoya Hamada and Atsushi Umehara",

note = "Funding Information: This work was financially supported by JSPS KAKENHI Grant Number JP20H02919. We are grateful to Dr Masahiro Hirama (Emeritus Professor of Tohoku University) for his encouragement. We also thank Mr. Daisuke Unabara (Tohoku University) for ESI-TOF/MS measurements, using a Bruker micrOTOF-Q II at Tagen Central Analytical Facility. Publisher Copyright: {\textcopyright} 2022 The Chemical Society of Japan.",

year = "2022",

month = may,

doi = "10.1246/bcsj.20220070",

language = "English",

volume = "95",

pages = "819--824",

journal = "Bulletin of the Chemical Society of Japan",

issn = "0009-2673",

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T1 - Convergent Synthesis of the HIJKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1 by a Late-Stage Reductive Olefin Coupling Approach

AU - Sasaki, Makoto

AU - Iwasaki, Kotaro

AU - Arai, Keisuke

AU - Hamada, Naoya

AU - Umehara, Atsushi

N1 - Funding Information: This work was financially supported by JSPS KAKENHI Grant Number JP20H02919. We are grateful to Dr Masahiro Hirama (Emeritus Professor of Tohoku University) for his encouragement. We also thank Mr. Daisuke Unabara (Tohoku University) for ESI-TOF/MS measurements, using a Bruker micrOTOF-Q II at Tagen Central Analytical Facility. Publisher Copyright: © 2022 The Chemical Society of Japan.

PY - 2022/5

Y1 - 2022/5

N2 - The convergent synthesis of the HIJKLMN-ring fragment of Caribbean ciguatoxin C-CTX-1, the major causative toxin for ciguatera fish poisoning in the Caribbean Sea and the Northeast Atlantic areas, is disclosed. The synthesis features a late-stage iron-catalyzed hydrogen atom transfer-initiated reductive olefin coupling to install the N-ring and a SuzukiMiyaura coupling/ thioacetalization strategy for the convergent assembly of the hexacyclic HIJKLM-ring skeleton.

AB - The convergent synthesis of the HIJKLMN-ring fragment of Caribbean ciguatoxin C-CTX-1, the major causative toxin for ciguatera fish poisoning in the Caribbean Sea and the Northeast Atlantic areas, is disclosed. The synthesis features a late-stage iron-catalyzed hydrogen atom transfer-initiated reductive olefin coupling to install the N-ring and a SuzukiMiyaura coupling/ thioacetalization strategy for the convergent assembly of the hexacyclic HIJKLM-ring skeleton.

KW - Caribbean ciguatoxin

KW - Convergent synthesis

KW - Cross coupling

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DO - 10.1246/bcsj.20220070

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AN - SCOPUS:85134539850

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JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

IS - 5

ER -

Convergent Synthesis of the HIJKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1 by a Late-Stage Reductive Olefin Coupling Approach

Abstract

Keywords

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