Convergent and Scalable Second-Generation Synthesis of the Fully Functionalized HIJKLMN-Ring Segment of Caribbean Ciguatoxin C-CTX-1Click to copy article linkArticle link copied!
- Makoto Sasaki*Makoto Sasaki*Email: [email protected]Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, JapanMore by Makoto Sasaki
- Miyu OhbaMiyu OhbaGraduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, JapanMore by Miyu Ohba
- Ako MurakamiAko MurakamiGraduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, JapanMore by Ako Murakami
- Atsushi UmeharaAtsushi UmeharaGraduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, JapanMore by Atsushi Umehara
Abstract
A highly convergent and scalable second-generation synthesis of the fully functionalized HIJKLMN-ring segment of Caribbean ciguatoxin C-CTX-1, the primary toxin responsible for ciguatera fish poisoning in the Caribbean Sea and the Northeast Atlantic regions, has been accomplished. Key aspects of the synthetic approach include the efficient syntheses of the HI- and KLM-ring fragments on gram scales, a convergent fragment coupling toward the HIJKLM-ring skeleton based on the Suzuki–Miyaura coupling strategy, and optimized iron hydride-catalyzed hydrogen atom transfer-mediated olefin coupling conditions for constructing the N-ring.
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This article is cited by 1 publications.
- Daisuke Sato, Makoto Sasaki, Atsushi Umehara. Stereocontrolled Synthesis of the Portimine Skeleton via Organocatalyst-Mediated Asymmetric Stannylation and Stereoretentive C(sp3)–C(sp2) Stille Coupling. Organic Letters 2025, 27
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, 942-947. https://doi.org/10.1021/acs.orglett.4c04245
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