Synthetic Approach toward (–)-Tetrodotoxin via Construction of the Bicyclo[2.2.2]octane Skeleton

Author:

Fukuyama Tohru,Yokoshima SatoshiORCID,Kobayashi Kazuki,Senoo Yoshiki,Toma Tatsuya

Abstract

AbstractA synthetic approach toward (–)-tetrodotoxin (TTX) is described. Our approach features a stereoselective construction of the TTX core structure using the bicyclo[2.2.2]octane skeleton which was constructed via intramolecular Diels–Alder reaction of an o-quinone monoketal having the key functional groups. The robust asymmetric synthesis was achieved by an iridium-catalyzed dynamic kinetic resolution (DKR) of the aryl vinyl carbinol that could be easily prepared from a simple aromatic compound.

Funder

Japan Society for the Promotion of Science

Japan Agency for Medical Research and Development

Ministry of Education, Culture, Sports, Science and Technology

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Cited by 1 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Looking Back on My Past;Journal of Synthetic Organic Chemistry, Japan;2023-02-01

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