Synthesis of α‐Chiral Butyrolactones by Highly Stereoselective Radical Transfer or Sequential Asymmetric Alkylations: Concise Preparation of Leupyrrin Moieties. Issue 45 (10th September 2015)

• Record Type: Journal Article
• Authors: Schrempp, Michael; Thiede, Sebastian; Herkommer, Daniel; Gansäuer, Andreas; Menche, Dirk
• Is Part Of: Chemistry. Volume 21:Issue 45(2015)
• Page Start: 16266
• Page End: 16271
• Publication Date: 2015-09-10
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201502263
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Inspired by the bioactive natural metabolites leupyrrin A₁ and B₁, two novel stereoselective methods for the highly concise synthesis of densely substituted α‐chiral butyrolactones are reported. The first approach relies on an innovative three‐step Ti^III‐catalyzed radical reaction that proceeds with excellent chemo‐, regio‐, and stereoselectivity. The alternative route utilizes sequential asymmetric alkylations and enables asymmetric synthesis of the authentic α‐tetrasubstituted butyrolactone motif of the leupyrrins in only four steps from commercially available substrates.</p> </abstract>