HIV Protease Inhibitors Part 2: [3+2] Cycloaddition, Isomerization; and Ring Expansion en route to 4,5-Substituted Cyclohexenones

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 cycloadduc...

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Bibliographic Details
Published in:Synlett 2004-03, Vol.2004 (4), p.684-687
Main Authors: Demont, Emmanuel, Eatherton, Andrew, Frampton, Christopher S., Kahn, Irfan, Redshaw, Sally
Format: Article
Language:English
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Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2004-815439