Petasis/Diels-Alder/cyclization cascade reactions for the generation of scaffolds with multiple stereogenic centers and orthogonal handles for library production

• Main Authors: Flagstad, Thomas, Azevedo, Carlos M. G., Min, Geanna, Willaume, Anthony, Morgentin, Rémy, Nielsen, Thomas E., Clausen, Mads Hartvig
• Other Authors: Singapore Centre for Environmental Life Sciences and Engineering
• Format: Article
• Language: English
• Published: 2020
• Subjects: Engineering::Environmental engineering; Petasis Reaction; Cycloaddition
• Online Access: https://hdl.handle.net/10356/140820
• Institution: Nanyang Technological University

A new effective strategy for the synthesis of sp3-rich small molecules for library production is presented. The key steps to generate complexity involve a Petasis three-component reaction followed by an intramolecular Diels–Alder and cyclization to generate a densely enriched tricyclic or tetracyclic scaffolds with 3–4 stereocenters and three handles for decoration. The strategy was used for the production of 143 molecules for the European Lead Factory.