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Large-scale synthesis of new pyranoid building blocks based on aldolase-catalysed carbon-carbon bond formation

: Wolberg, M.; Dassen, B.H.N.; Schürmann, M.; Jennewein, S.; Wubbolts, M.G.; Schoemaker, H.E.; Mink, D.


Advanced synthesis & catalysis 350 (2008), No.11-12, pp.1751-1759
ISSN: 1615-4150
ISSN: 1615-4169
Journal Article
Fraunhofer IME ()

A new large-scale approach to the synthetically versatile chloromethyl-substituted, alpha,beta-unsaturated delta-lactone 3 is described. The synthesis is based oil a blocatalytic process performed oil an industrial scale. Conjugate addition of G, 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 oil an attractive scale.