- Gold-Catalyzed Dehydrogenative Cycloisomerization of 1,4-Enyne Esters to 3,5-Disubstituted Phenol Derivatives
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A method to prepare synthetically important 3,5-disubstituted phenol derivatives that relies on the sequential gold(I)-catalyzed dehydrogenative cycloisomerization of 1,4-enyne esters in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) or N-fluorobenzenesulfonimide (NFSI) is described. The synthetic versatility of the methodology was exemplified by a gram-scale reaction of one example, the ease to realize subsequent functional transformations of an adduct, and the application of the method to the synthesis of the bioactive molecule LUF5771. (Figure presented.).
- Chen, Cuili,Chen, Xianxiao,Zhang, Xiaoxiang,Wang, Shifa,Rao, Weidong,Chan, Philip Wai Hong
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p. 4359 - 4368
(2017/12/26)
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- Synthesis of filibuvir. Part I. Diastereoselective preparation of a β-hydroxy alkynyl oxazolidinone and conversion to a 6,6- disubstituted 2H-pyranone
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This is the first in a series of three papers describing the identification and development of a commercial synthesis of filibuvir (1). This contribution describes development of an Evans aldol reaction to control the tertiary alcohol stereocenter, a challenging variant of that strategy in that both reacting partners were nonstandard (acetate enolate and ketone electrophile). A sequence consisting of Sonogashira coupling, acylation and hydrogenation delivered acetate 24, and Dieckmann cyclization provided β-keto lactone 2.
- Singer, Robert A.,Ragan, John A.,Bowles, Paul,Chisowa, Esmort,Conway, Brian G.,Cordi, Eric M.,Leeman, Kyle R.,Letendre, Leo J.,Sieser, Janice E.,Sluggett, Gregory W.,Stanchina, Corey L.,Strohmeyer, Holly,Blunt, Jon,Taylor, Stuart,Byrne, Ciaran,Lynch, Denis,Mullane, Sandra,O'Sullivan, Maria M.,Whelan, Marcella
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- INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME
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The invention relates to compounds of the formula (I) and to pharmaceutically acceptable salts, solvates, prodrugs and metabolites thereof, wherein W, Z, R1and R2, are as defined herein. The invention also relates to methods of treating Hepatitis C virus in mammals by administering the compounds of formula (I), and to pharmaceutical compositions for treating such disorders, which contain the compounds of formula (I). The invention also relates to methods of preparing the compounds of formula (I).
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- INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME
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Compounds of formula (I) are hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors, and are useful in therapeutic and prophylactic treatment of persons infected with hepatitis C virus.
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Page/Page column 57
(2010/02/07)
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- Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same
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Compounds of formula I are hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors, and are useful in therapeutic and prophylactic treatment of persons infected with hepatitis C virus.
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