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

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...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2015-11, Vol.21 (45), p.16266
Main Authors: Schrempp, Michael, Thiede, Sebastian, Herkommer, Daniel, Gansauer, Andreas, Menche, Dirk
Format: Article
Language:English
Subjects:
Chemistry
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201502263