Journal
TETRAHEDRON-ASYMMETRY
Volume 23, Issue 11-12, Pages 898-903Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2012.06.003
Keywords
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Funding
- CSIR
- DST, New Delhi [SR/S1/OC-67/2010]
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A short and efficient enantioselective synthesis of the HIV protease inhibitor amprenavir 1 (99% ee) as well as a formal synthesis of saquinavir 3 have been achieved in high enantiomeric purity starting from commercially available materials. Our strategy mainly comprises a Co-catalyzed two-stereocentred hydrolytic kinetic resolution (HKR) of racemic 2-(1-azido-2-phenylethyl)oxirane as the chirality inducing step. Also presented is a concise synthesis of (S)-3-hydroxytetrahydrofuran 4, the key structural feature, in high enantiomeric purity (98% ee). (c) 2012 Elsevier Ltd. All rights reserved.
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