Potential use of carbocyclic nucleosides for the treatment of AIDS: chemo-enzymatic syntheses of the enantiomers of carbovir
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 589-592
- https://doi.org/10.1039/p19920000589
Abstract
The lactam (1R),(4S)-2-azabicyclo[2.2.1]hept-5-en-3-one [(–)-2], derived by whole cell enantio-specific hydrolysis of the racemate was converted into (–)-carbovir (–)-1 in ten steps. Lipase catalysed acetylation of 4-cis-hydroxycyclopent-2-enylmethyl triphenylmethyl ether afforded the optically pure ester (+)-3 and the alcohol (–)-9. The former compound was converted into (+)-carbovir (+)-1 in three steps.Keywords
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