Generation of a Heteropolycyclic and Sp3-Rich Scaffold for Library Synthesis from a Highly Diastereoselective Petasis/DielsAlder and ROM-RCM Reaction Sequence

Thomas Flagstad, Carlos Azevedo, Nikolaj Sten Troelsen, Geanna Min, Yohan Macé, Anthony Willaume, Rachel Guilleux, Mélanie Velay, Karine Bonnet, Rémy Morgentin, Thomas E. Nielsen, Mads Hartvig Clausen*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

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Abstract

Efficient access to diverse screening compounds with desirable, lead-like properties can be a bottleneck in early drug discovery and chemical biology. Here we present an efficient, rapid route to three structurally distinct classes of compounds (A–C) from a single precursor, which in turn is available through a one-pot Petasis 3-component-reaction–Diels-Alder cascade reaction. We demonstrate the versatility of the approach through the synthesis of 35 exemplary compounds from the three classes, as well as by the production of 2188 final compounds, which have been included in the Joint European Compound Library of the European Lead Factory.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number5
Pages (from-to)1061-1076
Number of pages16
ISSN1434-193X
DOIs
Publication statusPublished - 2019

Keywords

  • Drug discovery
  • Heterocycles
  • Cycloaddition

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