Journal ArticleDOI
A stereoselective synthesis of (-)-tetrodotoxin.
Andrew Hinman,J. Du Bois +1 more
TLDR
In this article, an asymmetric synthesis of (−)-tetrodotoxin is described, which employs a number of unique transformations, foremost of which are two stereospecific C−H bond functionalization reactions.Abstract:
An asymmetric synthesis of the fugu fish poison, (−)-tetrodotoxin, is described. The route to this extraordinary target employs a number of unique transformations, foremost of which are two stereospecific C−H bond functionalization reactions. Accordingly, Rh-catalyzed carbene and nitrene C−H insertions facilitate rapid entry to the cyclohexane core of the natural product and make possible the late-stage installation of the tetrasubstituted carbinolamine center.read more
Citations
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Journal ArticleDOI
Marine natural products.
TL;DR: This review covers the literature published in 2014 for marine natural products, with 1116 citations referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms.
Journal ArticleDOI
Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation
TL;DR: This review focuses on Rh-catalyzed methods for C-H bond functionalization, which have seen widespread success over the course of the last decade and are discussed in detail in the accompanying articles in this special issue of Chemical Reviews.
Journal ArticleDOI
C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals
TL;DR: This Review provides an overview of C-H bond functionalization strategies for the rapid synthesis of biologically active compounds such as natural products and pharmaceutical targets.
Journal ArticleDOI
Palladium-catalyzed cross-coupling reactions in total synthesis.
TL;DR: In this Review, highlights of a number of selected syntheses are discussed, demonstrating the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.
Journal ArticleDOI
Catalytic C–H functionalization by metal carbenoid and nitrenoid insertion
TL;DR: Several facets of these kinds of C–H functionalization reactions are discussed and a perspective on how this methodology has affected the synthesis of complex natural products and potential pharmaceutical agents are provided.
References
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Journal ArticleDOI
Tarichatoxin--tetrodotoxin: a potent neurotoxin.
Journal ArticleDOI
A Rh‐Catalyzed C−H Insertion Reaction for the Oxidative Conversion of Carbamates to Oxazolidinones
Christine G. Espino,J. Du Bois +1 more
TL;DR: The reaction is stereospecific, providing access to chiral α-branched amines from optically pure starting materials with no loss in enantiomeric excess.
Journal ArticleDOI
The structure of tetrodotoxin
TL;DR: Tsuda and Kawamura as discussed by the authors isolated tetrodotoxin from the liver and ovaries of the tiger puffer (S. porphyreus) and achieved its isolation in a pure state.
Journal ArticleDOI
First Asymmetric Total Synthesis of Tetrodotoxin
TL;DR: This work has achieved the first asymmetric total synthesis from 2-acetoxy-tri-O-acetyl-d-glucal as a chiral starting material and selected the protective groups to accomplish the total synthesis of tetrodotoxin in an enantiomerically pure form.
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Catalytic C–H functionalization by metal carbenoid and nitrenoid insertion
A Rh‐Catalyzed C−H Insertion Reaction for the Oxidative Conversion of Carbamates to Oxazolidinones
Christine G. Espino,J. Du Bois +1 more