کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1350690 | 980457 | 2006 | 4 صفحه PDF | دانلود رایگان |
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.
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.Figure optionsDownload as PowerPoint slide
(S)-4-Hydroxy-3,5-dimethyl-5-((4E,6E)-3-oxoocta-4,6-dienyl)furan-2(5H)-oneC14H18O4Ee = 94%[α]D26=-25.8 (c 0.05, CHCl3)
Journal: Tetrahedron: Asymmetry - Volume 17, Issue 15, 11 September 2006, Pages 2195–2198