Journal
TETRAHEDRON
Volume 75, Issue 38, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.130513
Keywords
Lead-oriented synthesis; Molecular diversity; Molecular scaffolds
Categories
Funding
- EPSRC [EP/N025652/1]
- EPSRC [1939686, EP/N025652/1] Funding Source: UKRI
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The synthesis of large numbers of diverse molecular scaffolds with controlled molecular properties is a significant challenge in synthetic organic chemistry. A modular unified synthesis was developed, and was exploited in the synthesis of sixteen diverse three-dimensional scaffolds. The approach exploited two cyclisation precursors to be converted, using a toolkit of cyclisation reactions, into spirocyclic and fused ring scaffolds. Remarkably, Pd-catalysed aminoarylation of substituted N-Boc-hex-5-enylamine cyclisation precursors to yield N-Boc piperidine-containing scaffolds was successful which was ascribed to a significant Thorpe-Ingold effect. Computational property analysis showed that the decorated scaffolds are shape-diverse, and enable diverse lead-like chemical space to be targeted. (C) 2019 Published by Elsevier Ltd.
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