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

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...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2008-08, Vol.350 (11-12), p.1751-1759
Main Authors: Wolberg, Michael, Dassen, Ben H. N., Schürmann, Martin, Jennewein, Stefan, Wubbolts, Marcel G., Schoemaker, Hans E., Mink, Daniel
Format: Article
Language:English
Subjects:
aldolase
conjugate addition
enzymatic catalysis
large-scale synthesis
α-pyrones
δ-lactones
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200800224