Large-Scale Synthesis of New Pyranoid Building Blocks Based on Aldolase-Catalysed Carbon-Carbon Bond Formation

✍ Scribed by Michael Wolberg; Ben H. N. Dassen; Martin Schürmann; Stefan Jennewein; Marcel G. Wubbolts; Hans E. Schoemaker; Daniel Mink

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 249 KB
• Volume: 350
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.200800224

✦ Synopsis

Abstract

A new large‐scale approach to the synthetically versatile chloromethyl‐substituted, α,β‐unsaturated δ‐lactone 3 is described. The synthesis is based on a biocatalytic process performed on an industrial scale. Conjugate addition of C‐, N‐, O‐, and S‐nucleophiles to lactone 3 affords a variety of new pyranoid building blocks in a highly diastereoselective manner. The operational simplicity of the whole sequence allows for preparing these building blocks on an attractive scale.