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Synlett 2004(4): 679-683
DOI: 10.1055/s-2004-815438
DOI: 10.1055/s-2004-815438
LETTER
© Georg Thieme Verlag Stuttgart · New York
HIV Protease Inhibitor Part 1: Use of Evans’ Oxazolidinone in Intermolecular Diels-Alder Reaction en route to 3,4-Substituted Cyclohexanones
Further Information
Publication History
Received
12 January 2004
Publication Date:
29 January 2004 (online)


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