Tetrodotoxin Framework Construction from Linear Substrates Utilizing a Hg(OTf)2-Catalyzed Cycloisomerization Reaction: Synthesis of the Unnatural Analogue 11-nor-6,7,8-Trideoxytetrodotoxin

Keisuke Nishikawa; Takayuki Noguchi; Seiho Kikuchi; Takahiro Maruyama; Yusuke Araki; Mari Yotsu-Yamashita; Yoshiki Morimoto

doi:10.1021/acs.orglett.1c00125

Tetrodotoxin Framework Construction from Linear Substrates Utilizing a Hg(OTf)₂-Catalyzed Cycloisomerization Reaction: Synthesis of the Unnatural Analogue 11-nor-6,7,8-Trideoxytetrodotoxin

Keisuke Nishikawa, Takayuki Noguchi, Seiho Kikuchi, Takahiro Maruyama, Yusuke Araki, Mari Yotsu-Yamashita, Yoshiki Morimoto

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

5 Citations (Scopus)

Abstract

In this contribution, we propose a new synthetic approach to tetrodotoxin (TTX), one of the most famous marine toxins that, after first preparing a functionalized linear substrate, forms a cyclohexane core from the substrate utilizing our mercuric triflate (Hg(OTf)2)-catalyzed cycloisomerization reaction. The concept was applied to the synthesis of 11-nor-6,7,8-trideoxyTTX and 11-nor-4,9-anhydro-6,7,8-trideoxyTTX, which are unnatural TTX analogues, demonstrating the validity of our new approach.

Original language	English
Pages (from-to)	1703-1708
Number of pages	6
Journal	Organic letters
Volume	23
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.1c00125
Publication status	Published - 2021 Mar 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1021/acs.orglett.1c00125

Cite this

Nishikawa, K., Noguchi, T., Kikuchi, S., Maruyama, T., Araki, Y., Yotsu-Yamashita, M., & Morimoto, Y. (2021). Tetrodotoxin Framework Construction from Linear Substrates Utilizing a Hg(OTf)₂-Catalyzed Cycloisomerization Reaction: Synthesis of the Unnatural Analogue 11-nor-6,7,8-Trideoxytetrodotoxin. Organic letters, 23(5), 1703-1708. https://doi.org/10.1021/acs.orglett.1c00125

Tetrodotoxin Framework Construction from Linear Substrates Utilizing a Hg(OTf)₂-Catalyzed Cycloisomerization Reaction: Synthesis of the Unnatural Analogue 11-nor-6,7,8-Trideoxytetrodotoxin. / Nishikawa, Keisuke; Noguchi, Takayuki; Kikuchi, Seiho et al.
In: Organic letters, Vol. 23, No. 5, 05.03.2021, p. 1703-1708.

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

Nishikawa, K, Noguchi, T, Kikuchi, S, Maruyama, T, Araki, Y, Yotsu-Yamashita, M & Morimoto, Y 2021, 'Tetrodotoxin Framework Construction from Linear Substrates Utilizing a Hg(OTf)₂-Catalyzed Cycloisomerization Reaction: Synthesis of the Unnatural Analogue 11-nor-6,7,8-Trideoxytetrodotoxin', Organic letters, vol. 23, no. 5, pp. 1703-1708. https://doi.org/10.1021/acs.orglett.1c00125

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title = "Tetrodotoxin Framework Construction from Linear Substrates Utilizing a Hg(OTf)2-Catalyzed Cycloisomerization Reaction: Synthesis of the Unnatural Analogue 11-nor-6,7,8-Trideoxytetrodotoxin",

abstract = "In this contribution, we propose a new synthetic approach to tetrodotoxin (TTX), one of the most famous marine toxins that, after first preparing a functionalized linear substrate, forms a cyclohexane core from the substrate utilizing our mercuric triflate (Hg(OTf)2)-catalyzed cycloisomerization reaction. The concept was applied to the synthesis of 11-nor-6,7,8-trideoxyTTX and 11-nor-4,9-anhydro-6,7,8-trideoxyTTX, which are unnatural TTX analogues, demonstrating the validity of our new approach.",

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AU - Nishikawa, Keisuke

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AU - Morimoto, Yoshiki

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