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-initia...

Full description

Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan
Main Authors: Sasaki, Makoto, Iwasaki, Kotaro, Arai, Keisuke, Hamada, Naoya, Umehara, Atsushi
Format: Article in Journal/Newspaper
Language:English
Published: Oxford University Press (OUP) 2022
Subjects:
General Chemistry
Northeast Atlantic
Online Access:http://dx.doi.org/10.1246/bcsj.20220070
https://academic.oup.com/bcsj/article-pdf/95/5/819/56317859/bcsj.20220070.pdf
id croxfordunivpr:10.1246/bcsj.20220070
record_format openpolar
spelling croxfordunivpr:10.1246/bcsj.20220070 2024-03-03T08:47:18+00:00 Convergent Synthesis of the HIJKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1 by a Late-Stage Reductive Olefin Coupling Approach Sasaki, Makoto Iwasaki, Kotaro Arai, Keisuke Hamada, Naoya Umehara, Atsushi 2022 http://dx.doi.org/10.1246/bcsj.20220070 https://academic.oup.com/bcsj/article-pdf/95/5/819/56317859/bcsj.20220070.pdf en eng Oxford University Press (OUP) https://academic.oup.com/pages/standard-publication-reuse-rights Bulletin of the Chemical Society of Japan volume 95, issue 5, page 819-824 ISSN 0009-2673 1348-0634 General Chemistry journal-article 2022 croxfordunivpr https://doi.org/10.1246/bcsj.20220070 2024-02-05T10:35:25Z 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 Suzuki–Miyaura coupling/thioacetalization strategy for the convergent assembly of the hexacyclic HIJKLM-ring skeleton. Article in Journal/Newspaper Northeast Atlantic Oxford University Press Bulletin of the Chemical Society of Japan 95 5 819 824
institution Open Polar
collection Oxford University Press
op_collection_id croxfordunivpr
language English
topic General Chemistry
spellingShingle General Chemistry
Sasaki, Makoto
Iwasaki, Kotaro
Arai, Keisuke
Hamada, Naoya
Umehara, Atsushi
Convergent Synthesis of the HIJKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1 by a Late-Stage Reductive Olefin Coupling Approach
topic_facet General Chemistry
description 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 Suzuki–Miyaura coupling/thioacetalization strategy for the convergent assembly of the hexacyclic HIJKLM-ring skeleton.
format Article in Journal/Newspaper
author Sasaki, Makoto
Iwasaki, Kotaro
Arai, Keisuke
Hamada, Naoya
Umehara, Atsushi
author_facet Sasaki, Makoto
Iwasaki, Kotaro
Arai, Keisuke
Hamada, Naoya
Umehara, Atsushi
author_sort Sasaki, Makoto
title Convergent Synthesis of the HIJKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1 by a Late-Stage Reductive Olefin Coupling Approach
title_short Convergent Synthesis of the HIJKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1 by a Late-Stage Reductive Olefin Coupling Approach
title_full Convergent Synthesis of the HIJKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1 by a Late-Stage Reductive Olefin Coupling Approach
title_fullStr Convergent Synthesis of the HIJKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1 by a Late-Stage Reductive Olefin Coupling Approach
title_full_unstemmed Convergent Synthesis of the HIJKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1 by a Late-Stage Reductive Olefin Coupling Approach
title_sort convergent synthesis of the hijklmn-ring fragment of caribbean ciguatoxin c-ctx-1 by a late-stage reductive olefin coupling approach
publisher Oxford University Press (OUP)
publishDate 2022
url http://dx.doi.org/10.1246/bcsj.20220070
https://academic.oup.com/bcsj/article-pdf/95/5/819/56317859/bcsj.20220070.pdf
genre Northeast Atlantic
genre_facet Northeast Atlantic
op_source Bulletin of the Chemical Society of Japan
volume 95, issue 5, page 819-824
ISSN 0009-2673 1348-0634
op_rights https://academic.oup.com/pages/standard-publication-reuse-rights
op_doi https://doi.org/10.1246/bcsj.20220070
container_title Bulletin of the Chemical Society of Japan
container_volume 95
container_issue 5
container_start_page 819
op_container_end_page 824
_version_ 1792503471230943232

Similar Items