Multicomponent assembly processes for the synthesis of diverse yohimbine and corynanthe alkaloid analogues.

ACS Comb Sci

Department of Chemistry and Biochemistry, The Texas Institute for Drug and Diagnostic Development, The University of Texas at Austin, Austin, Texas 78712, United States.

Published: July 2013

A strategy involving a Mannich-type multicomponent assembly process followed by a 1,3-dipolar cycloaddition has been developed for the rapid and efficient construction of parent heterocyclic scaffolds bearing indole and isoxazolidine rings. These key intermediates were then readily elaborated using well-established protocols for refunctionalization and cross-coupling to access a diverse 180-member library of novel pentacyclic and tetracyclic compounds related to the Yohimbine and Corynanthe alkaloids. Several other new multicomponent assembly processes were developed to access dihydro-β-carboline-fused benzodiazepines, pyrimidinediones, and rutaecarpine derivatives.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3800219PMC
http://dx.doi.org/10.1021/co400055bDOI Listing

Publication Analysis

Top Keywords

multicomponent assembly
12
assembly processes
8
yohimbine corynanthe
8
processes synthesis
4
synthesis diverse
4
diverse yohimbine
4
corynanthe alkaloid
4
alkaloid analogues
4
analogues strategy
4
strategy involving
4

Similar Publications

Proton exchange membrane fuel cells (PEMFCs) are being pursued for applications in the maritime industry to meet stringent ship emissions regulations. Further basic research is needed to improve the performance of PEMFCs in marine environments. Assembly stress compresses the gas diffusion layer (GDL) beneath the ribs, significantly altering its pore structure and internal transport properties.

View Article and Find Full Text PDF

Polynuclear Au(I) cluster photocatalysts, known for their high activity and stability, hold substantial potential in organic synthetic chemistry. This study synthesized two Au(I) supramolecular cluster catalysts with different nuclearities: a tetranuclear cluster, C1 ([(dppmAu2)2L1]•PF6-), and a hexadecanuclear cluster, C2 [(dppmAu2)6(Au4)(L1)4]•4PF6-, through a multicomponent stepwise self-assembly approach. Both cluster structures feature aurophilicity interaction motifs that endow them with exceptional photocatalytic performance, exhibiting optical band gaps of 2.

View Article and Find Full Text PDF

Micron-scale colloidal particles with short-ranged attractions, e.g., colloids functionalized with single-stranded DNA oligomers, have emerged as a powerful platform for studying colloidal self-assembly phenomena with the long-term goal of identifying routes for metamaterial fabrication.

View Article and Find Full Text PDF

Noncovalently Bridging Cell-Surface Proteins Using Synthetic Peptides to Modulate Cell Apoptosis.

Nano Lett

December 2024

Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.

Controlled high-order clustering of cell-surface proteins is an essential but unmatched regulatory mechanism in living systems for the modulation of cell behavior. Here, we present a strategy for generating extended and tunable one-dimensional clusters of death receptors on live cell surfaces by employing synthetic peptides to noncovalently bridging the proteins. The on-cell assembly process is validated through super-resolution fluorescence imaging and fluorescence lifetime imaging analyses.

View Article and Find Full Text PDF

Multinuclear Antimony-Bismuth-Lanthanide Cluster-Connected Polyoxometalate for the Detection of 5-Hydroxyindoleacetic Acid via Luminescence.

Inorg Chem

December 2024

Henan Key Laboratory of Polyoxometalate Chemistry, College of Chemistry and Molecular Sciences, Henan University, Kaifeng, Henan 475004, China.

The judicious selection and combination of multicomponents provide great potential for the further exploration of new polyoxometalate (POM) materials. Here, a delicate control on tungstate, Sb and Bi sources, Eu ions, and organic molecules led to the discovery of a novel multimetal cluster-embedded POM [HN(CH)]NaH{[Eu(HO)SbBiWO](SbWO)(SbWO)}·78HO (). The polyoxoanion of was constructed from four in situ-formed [SbWO] and [SbWO] building blocks connected by two hexa-metallic [Eu(HO)SbBiWO] clusters, to be a rare member of Sb- and Bi-coexisting POM.

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!