The present invention provides novel methods for the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one of formula (VI-i) STR1 which is useful as a human immunodeficiency virus (HIV) reverse transcriptase inhibitor.
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(2008/06/13)
Asymmetric synthesis of benzoxazinones
The present invention provides novel methods for the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one of formula (VI-i) STR1 which is useful as a human immunodeficiency virus (HIV) reverse transcriptase inhibitor.
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(2008/06/13)
Practical asymmetric synthesis of Efavirenz (DMP 266), an HIV-1 reverse transcriptase inhibitor
A highly enantioselective and practical synthesis of the HIV-1 reverse transcriptase inhibitor efavirenz (1) is described. The synthesis proceeds in 62% overall yield in seven steps from 4-chloroaniline (6) to give efavirenz (1) in excellent chemical and optical purity. A novel, enantioselective addition of Li-cyclopropyl acetylide (4a) to p-methoxybenzyl-protected ketoaniline 3a mediated by (1R,2S)-N-pyrrolidinylnorephedrine lithium alkoxide (5a) establishes the stereogenic center in the target with a remarkable level of stereocontrol.
Pierce, Michael E.,Parsons Jr., Rodney L.,Radesca, Lilian A.,Lo, Young S.,Silverman, Stuart,Moore, James R.,Islam, Qamrul,Choudhury, Anusuya,Fortunak, Joseph M. D.,Nguyen, Dieu,Luo, Chi,Morgan, Susan J.,Davis, Wayne P.,Confalone, Pat N.,Chen, Cheng-Yi,Tillyer, Richard D.,Frey, Lisa,Tan, Lushi,Xu, Feng,Zhao, Dalian,Thompson, Andrew S.,Corley, Edward G.,Grabowski, Edward J. J.,Reamer, Robert,Reider, Paul J.
p. 8536 - 8543
(2007/10/03)
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