Lipase-catalyzed kinetic resolution of tetronic acid derivatives bearing a chiral quaternary carbon: total synthesis of ( S)-(−)-vertinolide

Both enantiomers were obtained with high enantiomeric excess by lipase-catalyzed kinetic resolution of tetronic acid derivatives. Total synthesis of ( S)-vertinolide from ( S)-alcohol was achieved in 33% yield in five steps. We have developed a chemoenzymatic synthesis of ( S)-vertinolide 1 with a c...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2006-09, Vol.17 (15), p.2195-2198
Main Authors: Tauchi, Tetsuo, Sakuma, Hiroki, Ohno, Takahiro, Mase, Nobuyuki, Yoda, Hidemi, Takabe, Kunihiko
Format: Article
Language:English
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Summary:Both enantiomers were obtained with high enantiomeric excess by lipase-catalyzed kinetic resolution of tetronic acid derivatives. Total synthesis of ( S)-vertinolide from ( S)-alcohol was achieved in 33% yield in five steps. We have developed a chemoenzymatic synthesis of ( S)-vertinolide 1 with a chiral quaternary carbon atom at C5. In the kinetic resolution of tetronic acid precursor 6, lipase PS-D furnished the recovered alcohol 6 with an ( R)-stereochemistry in a ratio of 95% ee, whereas lipase AY gave ( S)-alcohol 6 with 93% ee. Chemical transformations of ( S)-alcohol 6 provided ( S)-vertinolide 1 in 33% yield in five steps with no loss of enantiomeric excess.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2006.07.044