914800-59-2Relevant academic research and scientific papers
Large-scale synthesis of new pyranoid building blocks based on aldolase-catalysed carbon-carbon bond formation
Wolberg, Michael,Dassen, Ben H. N.,Schuermann, Martin,Jennewein, Stefan,Wubbolts, Marcel G.,Schoemaker, Hans E.,Mink, Daniel
, p. 1751 - 1759 (2008)
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.
