Unravelling the Synthesis and Chemistry of Stable, Acyclic, and Double‐Deficient 1, 3‐Butadienes: An endo‐Selective Diels–Alder Route to Hedgehog Pathway Inhibitors. Issue 11 (29th January 2019)

• Record Type: Journal Article
• Authors: Xin, Xiaoyi; Zimmermann, Stefan; Flegel, Jana; Otte, Felix; Knauer, Lena; Strohmann, Carsten; Ziegler, Slava; Kumar, Kamal
• Is Part Of: Chemistry. Volume 25:Issue 11(2019)
• Page Start: 2717
• Page End: 2722
• Publication Date: 2019-01-29
• Subjects: 1, 3-butadienes -- allenes -- Diels–Alder reaction -- dienes -- phosphine catalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201805823
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The first synthetic access to stable and acyclic 1, 3‐butadienes with two electron‐withdrawing carbonyl groups and their potential to deliver new molecular scaffolds through intriguing endo ‐selective Diels–Alder cycloadditions are presented. The bicyclic scaffolds produced through the cycloaddition chemistry of electron‐deficient dienes afforded potent Hedgehog signaling pathway inhibitors. Abstract : Uniquely deficient ! A facile synthetic access to stable, electron‐deficient and acyclic 1, 3‐butadienes bearing two orthogonal electron‐withdrawing groups is presented. This method opens the door to many molecular frameworks, including new Hedgehog pathway inhibitors.