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

被引：9

作者：

Nishikawa, Keisuke ^{[1
]}

Noguchi, Takayuki ^{[1
]}

Kikuchi, Seiho ^{[1
]}

Maruyama, Takahiro ^{[1
]}

Araki, Yusuke ^{[1
]}

Yotsu-Yamashita, Mari ^{[2
]}

Morimoto, Yoshiki ^{[1
]}

机构：

[1] Osaka City Univ, Grad Sch Sci, Dept Chem, Osaka 5588585, Japan

[2] Tohoku Univ, Grad Sch Agr Sci, Sendai, Miyagi 9808572, Japan

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 05期

关键词：

D O I：

10.1021/acs.orglett.1c00125

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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-trideoryTTX, which are unnatural TTX analogues, demonstrating the validity of our new approach.

引用

页码：1703 / 1708

页数：6

共 2 条

[1] Total Synthesis of (-)-Lepadiformine A Utilizing Hg(OTf)2-Catalyzed Cycloisomerization Reaction
Nishikawa, Keisuke
Kikuchi, Seiho
Ezaki, Shinnosuke
Koyama, Tomoyuki
Nokubo, Haruka
Kodama, Takeshi
Tachi, Yoshimitsu
Morimoto, Yoshiki
ORGANIC LETTERS, 2015, 17 (23) : 5772 - 5775
[2] One-Step Synthesis of the 1-Azaspiro[5.5]undecane Skeleton Characteristic of Histrionicotoxin Alkaloids from Linear Substrates via Hg(OTf)2-Catalyzed Cycloisomerization
Matsumura, Kunihiro
Nishikawa, Keisuke
Yoshida, Hiroaki
Niwa, Toshiki
Fushii, Yuichiro
Doe, Matsumi
Morimoto, Yoshiki
CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (14) : 1882 - 1886

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