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

نویسندگان

چکیده

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

برای دانلود باید عضویت طلایی داشته باشید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Enantioselective synthesis of highly substituted furans by a copper(II)-catalyzed cycloisomerization-indole addition reaction.

A catalytic enantioselective reaction based on a copper(II) catalyst strictly containing chiral anionic ligands is described. In the present work, copper(II)-phosphate catalyst promotes the intramolecular heterocyclization of 2-(1-alkynyl)-2-alkene-1-ones and facilitates high levels of enantioselectivity in the subsequent nucleophile attack. Mechanistic studies suggest that formation of a coppe...

متن کامل

Ga(III)-catalyzed cycloisomerization strategy for the synthesis of icetexane diterpenoids: total synthesis of (+/-)-salviasperanol.

[reaction: see text] A general approach to the tricyclic core of the icetexane natural products via the cycloisomerization of alkynyl indenes using GaCl(3) is presented. This strategy provides an efficient synthesis of the natural product salviasperanol and sets the stage for access to other members of this family of diterpenoids.

متن کامل

Synthesis of open chain analogue of 1,8-dioxooctahydroxanthene catalyzed by aluminosilicate MCM- 41

In this study, aluminosilicate MCM-41 has been found to be an efficient catalyst for reaction betweendifferent benzaldehyde derivatives and 5,5-dimethyl-1,3-cyclohexanedione to give open chain analogue of1,8-dioxo-octahydroxanthene in excellent yields. No evidence for the formation of cyclization products wasobserved. The catalyst can be used several times after recovery.

متن کامل

from linguistics to literature: a linguistic approach to the study of linguistic deviations in the turkish divan of shahriar

chapter i provides an overview of structural linguistics and touches upon the saussurean dichotomies with the final goal of exploring their relevance to the stylistic studies of literature. to provide evidence for the singificance of the study, chapter ii deals with the controversial issue of linguistics and literature, and presents opposing views which, at the same time, have been central to t...

15 صفحه اول

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

ژورنال

عنوان ژورنال: Organic Letters

سال: 2021

ISSN: ['1523-7060', '1523-7052']

DOI: https://doi.org/10.1021/acs.orglett.1c00125