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HIV Protease Inhibitors Part 2: [3+2] Cycloaddition, Isomerization; and Ring Expansion en route to 4,5-Substituted Cyclohexenones
- Source :
- Synlett. :684-687
- Publication Year :
- 2004
- Publisher :
- Georg Thieme Verlag KG, 2004.
-
Abstract
- 4,5-Substituted cyclohexanone 10 and its derivatives are carbocyclic analogues of Indinavir 3 and are expected to have antiviral activity. Early attempts to obtain these compounds via a diastereoselective [3+2] cycloaddition between 19 and 14 failed due to the sensitivity of the cycloadduct 24. It proved possible to obtain 30 from the α,β-unsaturated ester 27: [3+2] cycloaddition, isomerization, and ring expansion provided α,β-unsaturated ketone 31 from ester 26 in good yields. Further transformations of 31 gave the hydroxyethylamino inhibitor analogues of Indinavir 3.
Details
- ISSN :
- 14372096 and 09365214
- Database :
- OpenAIRE
- Journal :
- Synlett
- Accession number :
- edsair.doi...........e5d5ecd58c854db3fd2974d59480f910