135999-61-0Relevant articles and documents
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
experimental part, p. 1751 - 1759 (2009/07/25)
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.
Asymmetric synthesis of S-(+)-argentilactone and S-(-)-goniothalamin
Job,Wolberg,Müller,Enders
, p. 1796 - 1798 (2007/10/03)
The asymmetric synthesis of an α,β-unsaturated δ-lactone equivalent 8 as a key intermediate towards the total synthesis of a variety of natural products bearing such structural motifs is reported. An enzymatic approach was applied to provide both enantiomers of compound 8 using recLBADH (ee > 99%) and baker's yeast (ee = 94%), respectively. The utility of the intermediate was demonstrated by the total synthesis of the non-natural enantiomers of argentilactone [(S)-1] and goniothalamin [(S)-2].
Lipase-catalyzed asymmetric synthesis of 6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-ones and their conversion to chiral 5,6-epoxyhexanoates
Sakaki,Sakoda,Sugita,Sato,Kaneko
, p. 343 - 346 (2007/10/02)
Highly enantioselective syntheses of (R)- and (S)-6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-ones by means of lipase-catalyzed kinetic resolutions are described. Chiral dioxinones thus obtained have been converted to optically active 5,6-epoxyhexanoates, which are important precursors for a series of biologically active compounds.
