Cyclotrimerization strategy toward analogues of amaryllidaceae constituents. synthesis of deoxygenated pancratistatin core.

Org Lett

Department of Chemistry and Centre for Biotechnology, Brock University, St. Catharines, Ontario L2S 3A1, Canada.

Published: December 2005

[chemical reaction: see text]. A derivative of pancratistatin having no oxygenation in the aromatic ring was synthesized by a new strategy based on the cobalt-catalyzed cyclotrimerization of acetylenes as a prelude to diversity-oriented synthesis of further analogues.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol052372oDOI Listing

Publication Analysis

Top Keywords

cyclotrimerization strategy
4
strategy analogues
4
analogues amaryllidaceae
4
amaryllidaceae constituents
4
constituents synthesis
4
synthesis deoxygenated
4
deoxygenated pancratistatin
4
pancratistatin core
4
core [chemical
4
[chemical reaction
4

Similar Publications

Pinwheel-like Curved Aromatics from the Cyclotrimerization of Strained Alkyne Cycloparaphenylenes.

J Am Chem Soc

November 2024

Department of Chemistry and Biochemistry, Materials Science Institute, and Knight Campus for Accelerating Scientific Impact, University of Oregon, Eugene, Oregon 97403, United States.

Carbon nanomaterials composed of curved aromatics, such as carbon nanotubes, are difficult to selectively synthesize and modify precisely. Smaller molecular fragments of curved nanomaterials, such as cycloparaphenylenes, benefit from the precision of bottom-up synthesis, however, efforts to expand the curved molecular framework into even larger structures often rely on restrictive early stage synthetic strategies or difficult to control polymerizations. In this work we report a high yielding, strain-promoted, late-stage modification of a series of [ + 1]CPPs.

View Article and Find Full Text PDF

We introduce the first mechanochemical cyclotrimerization of nitriles, a facile strategy for synthesizing triazine-containing molecules and materials, overcoming challenges related to carbonization and solubility. Conducting this solid-state approach in a mixer ball mill with 4-Methylbenzonitrile, we synthesize Tris(4-methylphenyl)-1,3,5-triazine quantitatively in as little as 90 minutes. Just as fast, this mechanochemical method facilitates the synthesis of the covalent triazine framework CTF-1 using 1,4 Dicyanobenzene.

View Article and Find Full Text PDF

Here, an Ir/Zn-cocatalyzed atroposelective [2+2+2] cycloaddition of 1,6-diynes and ynamines was developed, forging various functionalized C─N axially chiral indoles and pyrroles in generally good to excellent yields (up to 99%), excellent chemoselectivities, and high enantioselectivities (up to 98% enantiomeric excess) with wide substrate scope. This cocatalyzed strategy not only provided an alternative promising and reliable way for asymmetric alkyne [2+2+2] cyclotrimerization in an easy handle but also settled the issues of previous [Rh(COD)]BF-catalyzed system on the construction of C─N axial chirality such as complex operations, limited substrate scope, and low efficiency. In addition, control experiments and theoretical calculations disclosed that Zn(OTf) markedly reduced the barrier of migration insertion to significantly increase reaction efficiency, which was distinctly different from previous work on the Lewis acid for improving reaction yield through accelerating oxidative addition and reductive elimination.

View Article and Find Full Text PDF

A highly proton conductive perfluorinated covalent triazine framework via low-temperature synthesis.

Nat Commun

December 2023

School of Chemical Engineering and Technology, Xi'an Jiaotong University, No. 28, Xianning West Road, Xi'an, Shaanxi, 710049, China.

Proton-conducting materials are essential to the emerging hydrogen economy. Covalent triazine frameworks (CTFs) are promising proton-conducting materials at high temperatures but need more effective sites to strengthen interaction for proton carriers. However, their construction and design in a concise condition are still challenges.

View Article and Find Full Text PDF

The polymerization property of aromatic polynitroso compounds could be used to create azodioxy porous networks with possible application for the adsorption of CO, the main greenhouse gas. Herein, we report the synthesis and characterization of new aromatic polynitroso compounds, with -nitroso groups attached to the triphenylbenzene, triphenylpyridine, triphenyltriazine and triphenylamine moiety. The synthesis of the pyridine-based trinitroso compound was performed by reduction of the corresponding trinitro derivative to -arylhydroxylamine followed by oxidation to the trinitroso product.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!