- Stereoselective synthesis of the epicoccin core
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A short, convergent, and asymmetric synthesis of the epicoccin core was achieved using a phosphite-promoted one-step condensation of a complex proline-type amino acid. Key features of the assembly of this amino acid were a double-bond isomerlzation/vlnylation/ring-closing metathesis strategy as well as an efficient, highly deastereoselective [2 + 2] cycloaddition of a ketene to an enecarbamate, derived from L-pyroglutamic acid.
- Gross, Ulrike,Nieger, Martin,Braese, Stefan
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Read Online
- HEPATITIS C VIRUS INHIBITORS
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The present invention discloses compounds of Formula (I), and pharmaceutically acceptable salts, esters, or prodrugs thereof: (structurally represented), which inhibit RNA-containing virus, particularly the hepatitis C virus (HCV). Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.
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Page/Page column 70
(2015/02/25)
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- A unified strategy targeting the thiodiketopiperazine mycotoxins exserohilone, gliotoxin, the epicoccins, the epicorazines, rostratin a and aranotin
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A unified synthetic strategy directed towards mycotoxins belonging to the thiodiketopiperazine family is reported. The building blocks for a number of natural products-including exserohilone, gliotoxin, the epicoccins, the epicorazines, rostratin A and aranotin-have been synthesised stereoselectively from a common precursor. This key intermediate was constructed through an efficient and highly diastereoselective[2+2] cycloaddition between a ketene and an enecarbamate derived from l-pyroglutamic acid. The annelation of the second ring was accomplished through ring-closing metathesis and enol ether-olefin ring-closing metathesis to provide both cis-and trans-annelated azabicyclic cyclohexenones, as well as an annelated sevenmembered cyclic enol ether. A Pd-catalysed elimination of allyl acetate gave rise to the cyclohexadienol structure of gliotoxin. Dimerisation of one building block to afford the diketopiperazine core was demonstrated.
- Gross, Ulrike,Nieger, Martin,Br?se, Stefan
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supporting information; experimental part
p. 11624 - 11631
(2010/11/17)
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- Synthesis of alexine-like compounds from chiral five-membered endocyclic enecarbamates
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Stereoselective syntheses of enantiomerically enriched trihydroxy pyrrolizidine and indolizidines were accomplished from a common chiral endocyclic enecarbamate. The synthetic strategy features an efficient [2+2] cycloaddition of ketenes to the endocyclic enecarbamate and a highly regioselective Baeyer-Villiger oxidation of the intermediate azabicyclic-cyclobutanones. These new heterocycles are compounds structurally related to the alexines.
- Valle, Marcelo Siqueira,Retailleau, Pascal,Correia, Carlos Roque Duarte
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p. 1957 - 1960
(2008/09/19)
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