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Full Paper
Large-Scale Synthesis of New Pyranoid Building Blocks Based on Aldolase-Catalysed Carbon-Carbon Bond Formation
Article first published online: 23 JUL 2008
DOI: 10.1002/adsc.200800224
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Wolberg, M., Dassen, B. H. N., Schürmann, M., Jennewein, S., Wubbolts, Marcel G., Schoemaker, Hans E. and Mink, D. (2008), Large-Scale Synthesis of New Pyranoid Building Blocks Based on Aldolase-Catalysed Carbon-Carbon Bond Formation. Adv. Synth. Catal., 350: 1751–1759. doi: 10.1002/adsc.200800224
Publication History
- Issue published online: 31 JUL 2008
- Article first published online: 23 JUL 2008
- Manuscript Received: 12 APR 2008
Keywords:
- aldolase;
- conjugate addition;
- enzymatic catalysis;
- δ-lactones;
- large-scale synthesis;
- α-pyrones
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.