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MiniBlock XT opens the door to sp3-rich tricyclic amine scaffolds through Diels-Alder reactions of azide-containing silyloxydienes

A library of 95 potential Sigma-1 and Sigma-2 inhibitors was swiftly generated taking advantage of the parallel synthesis capabilities of MiniBlock XT.

An elegant and divergent synthesis scheme was designed to prepare a series of analogs of potentially bioactive compounds. A 6,6,6-tricyclic amine building block was prepared through a Diels-Alder cycloaddition/Schmidt rearrangement domino sequence. Taking advantage of the MiniBlock XT unique capabilities in parallel synthesis, this scaffold was derivatized into 5 classes of analogs, for a total of 95 novel compounds. These structures will be screened against the Sigma-1 and Sigma-2 receptors to determine their biological activities.

Keywords:
Bioactive compounds, Diels-Alder, Schmidt, parallel synthesis

> SiliCycle MiniBlock XT Parrallel Synthesizer

Publication Efficient access to sp3-rich tricyclic amine scaffolds through Diels-Alder reactions of azide-containing silyloxydienes
Authors Michael C. McLeod, Jeffrey Aubé
Organization Department of Medicinal Chemistry, University of Kansas
Source Tetrahedron (2016), doi: 10.1016/j.tet.2016.03.016
Date 2016
Reaction scheme Efficient access to sp3-rich tricyclic amine scaffolds through Diels-Alder reactions of azide-containing silyloxydienes
Full publication http://www.sciencedirect.com/science/article/pii/S004040201630148X

 

SiliCycle MiniBlock XT

The SiliCycle MiniBlock XT is an easy-to-operate parallel synthesis system designed for synthesis and screening reactions. Applications include synthesis of small organic molecules, optimization of critical process parameters, and screening for optimal reaction conditions.

  • Parallel Synthesis
  • Reaction Screening
  • Catalyst Screening
  • Reflux and Inerting

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