Details

Autor(en) / Beteiligte

• Schrempp, Michael
• Thiede, Sebastian
• Herkommer, Daniel
• Gansauer, Andreas
• Menche, Dirk

Titel

Synthesis of [alpha]-Chiral Butyrolactones by Highly Stereoselective Radical Transfer or Sequential Asymmetric Alkylations: Concise Preparation of Leupyrrin Moieties

Ist Teil von

• Chemistry : a European journal, 2015-11, Vol.21 (45), p.16266

Ort / Verlag

Weinheim: Wiley Subscription Services, Inc

Erscheinungsjahr

2015

Link zum Volltext

Quelle

Wiley Online Library Journals Frontfile Complete

Beschreibungen/Notizen

• Inspired by the bioactive natural metabolites leupyrrinA1 and B1, two novel stereoselective methods for the highly concise synthesis of densely substituted [alpha]-chiral butyrolactones are reported. The first approach relies on an innovative three-step TiIII-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 [alpha]-tetrasubstituted butyrolactone motif of the leupyrrins in only four steps from commercially available substrates.