01350nas a2200169 4500008004100000022001400041245012500055210006900180260010600249300001200355490000700367520061100374100002300985700002001008700002201028856013001050 2012 eng d a0957-416600aEnantioselective synthesis of HIV protease inhibitor amprenavir via Co-catalyzed HKR of 2-(1-azido-2-phenylethyl)oxirane0 aEnantioselective synthesis of HIV protease inhibitor amprenavir aTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLANDbPERGAMON-ELSEVIER SCIENCE LTDcJUN a898-9030 v233 a
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.
1 aGadakh, Sunita, K.1 aReddy, Santhosh1 aSudalai, Arumugam uhttp://library.ncl.res.in/content/enantioselective-synthesis-hiv-protease-inhibitor-amprenavir-co-catalyzed-hkr-2-1-azido-2-0