Petasis/Diels-Alder/Cyclization Cascade Reactions for the Generation of Scaffolds with Multiple Stereogenic Centers and Orthogonal Handles for Library Production

Thomas Flagstad, Carlos M. G. Azevedo, Geanna Min, Anthony Willaume, Rémy Morgentin, Thomas E. Nielsen, Mads H. Clausen*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

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Abstract

A new effective strategy for the synthesis of sp3‐rich small molecules for library production is presented. The key steps to generate complexity highlight Petasis 3‐component reaction followed by an intramolecular Diels‐Alder and cyclization to generate a densely enriched tricyclic or tetracyclic scaffolds with 3‐4 stereocenters with 3 handles for decoration. The strategy was used for the production of 143 molecules for the European Lead Factory.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number36
Pages (from-to)5023-5029
Number of pages8
ISSN1434-193X
DOIs
Publication statusPublished - 2018

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