Samarium-promoted coupling of pyridine-based heteroaryl analogues of benzylic acetates with carbonyl compounds.

Org Lett

Department of Chemistry and Biochemistry and Walther Cancer Research Center, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, IN 46556, USA.

Published: August 2005

2-Substituted pyridine, quinoline, isoquinoline, bipyridine, and 1,10-phenanthroline analogues of benzylic acetates undergo SmI(2)-promoted coupling with aldehydes and ketones to afford (2-hydroxyalkyl)heteroaromatics. [reaction: see text]

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol050944zDOI Listing

Publication Analysis

Top Keywords

analogues benzylic
8
benzylic acetates
8
samarium-promoted coupling
4
coupling pyridine-based
4
pyridine-based heteroaryl
4
heteroaryl analogues
4
acetates carbonyl
4
carbonyl compounds
4
compounds 2-substituted
4
2-substituted pyridine
4

Similar Publications

Conformationally Restricted Grp94-Selective Inhibitors.

ACS Omega

January 2025

Department of Chemistry and Biochemistry, Warren Center for Drug Discovery, The University of Notre Dame, 305 McCourtney Hall, Notre Dame, Indiana 46556, United States.

Selective inhibition of glucose regulated protein 94 (Grp94), the most structurally unique isoform of heat shock protein 90 (Hsp90), has been implicated in the treatment of various disease states, including primary open-angle glaucoma and metastatic cancer. In this study, nine analogues were designed and synthesized by conformationally restricting , a second generation Grp94-selective inhibitor. Conformational constraints were applied to restrict the rotatable bonds and to bias the benzyl moiety into the Grp94 site 1 pocket as well as to reduce the entropic penalty paid upon binding.

View Article and Find Full Text PDF

Presented herein is the chemical construction of unprecedented 3,4-trans-3,6-anhydro hexofuranose frameworks. The disfavored 3,6-anhydro hexofuranosides were effectively established by Pd-catalyzed debenzylative intramolecular acetalation for the first time. The critical roles of benzyl protection and Pd as catalyst were demonstrated.

View Article and Find Full Text PDF

Synthesis of 2-hydroxy analogues of castanospermine, 1-epi-castanospermine and their iminooctitols from sugar-derived lactam.

Carbohydr Res

January 2025

Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Thiruvananthapuram, 695019, Kerala, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India. Electronic address:

The synthesis of 2-hydroxy analogues of castanospermine from two new iminooctitols via Mitsunobu cyclization is described. The iminooctitols were derived from the dihydroxylation of an allyl alcohol intermediate, obtained by adding vinylmagnesium bromide to the C6-aldehyde of a protected 1-deoxynojirimycin. An orthogonally protected hemiacetal with silyl group at the C6-hydroxy position and remaining as benzyl ethers, synthesized in four steps from d-glucose, served as a building block in the synthesis of the 1-deoxynojirimycin intermediate.

View Article and Find Full Text PDF

Synthesis and Characterization of a 1,2,4-Diazarsolide Anion.

Organometallics

January 2025

Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, United Kingdom.

Cyclopentadienyl anions ([Cp]) are pervasive ligands in coordination chemistry. In contrast, heavy-element derivatives of these ligands, particularly those that feature arsenic, are not as well developed. In this work, a new arsenic-based heterocycle with a structure analogous to [Cp] is presented.

View Article and Find Full Text PDF

In recent research, quinoline and indole structures have gained recognition for their significant clinical relevance and effectiveness. These compounds are known for their wide-ranging pharmacological effects, which include anticancer, antibacterial, antifungal, antiviral, and anti-inflammatory properties. Researchers have successfully implemented a variety of innovative synthetic strategies, leading to the creation of numerous compounds that display fascinating biological activities in diverse fields.

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!