Abstract
α,β-Unsaturated chiral oxazolidinone 10 can be smoothly obtained from the corresponding aldehyde 14 under Masamune-Roush conditions. Oxazolidinone 10 reacts diastereoselectively with diene 14 under lewis acid catalysis which allows the synthesis of 3,4-substituted cyclohexanone 16 and its derivatives 20 , 21 , and 22 in good overall yields from ester 4 . These compounds can be converted to the corresponding hydroxyethylamine derivatives, analogues of Saquinavir 1 , which are known to have antiviral activity.
Key words
oxazolidinone - Diels-Alder - cyclohexanone - cyclohexane - HIV protease inhibitor
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