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Total Synthesis of Tetrodotoxin.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2020 Apr 06; Vol. 59 (15), pp. 6253-6257. Date of Electronic Publication: 2020 Feb 19. - Publication Year :
- 2020
-
Abstract
- A total synthesis of tetrodotoxin was accomplished. A Diels-Alder reaction between a known enone and a siloxy diene gave a tricyclic product, the steric bias of which was used to construct the remaining stereogenic centers. A nitrogen atom was introduced either by a four-step sequence involving a Curtius rearrangement, or a three-step sequence featuring a newly developed transformation of a terminal alkyne into a nitrile. Introduction of the guanidine moiety followed by the formation of the heterocyclic system by cascade reactions led to tetrodotoxin.<br /> (© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 59
- Issue :
- 15
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 31985136
- Full Text :
- https://doi.org/10.1002/anie.201916611