Abstract:A new large-scale approach to the synthetically versatile chloromethyl-substituted, a,b-unsaturated d-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.

Formation. -The α,β-unsaturated δ-lactone (I) is subjected to the diastereoselective reaction with various S-, N-, O-and C-nucleophiles. Further transformations of building blocks (IIIa) and (IIIc) are demonstrated. -(WOLBERG*, M.; DASSEN, B. H. N.; SCHUERMANN, M.; JENNEWEIN, S.; WUBBOLTS, M. G.; SCHOEMAKER, H. E.; MINK, D.; Adv. Synth. Catal. 350 (2008) 11-12, 1751-1759; DSM Pharma Chem. Regensburg, D-93055 Regensburg, Germany; Eng.) -Y. Steudel 52-139

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