138760-82-4Relevant academic research and scientific papers
Stereoselective synthesis of 3,6-disubstituted-3,6-dihydropyridin-2-ones as potential diketopiperazine mimetics using organocopper-mediated anti-S N2′ reactions and their use in the preparation of low-molecule CXCR4 antagonists
Niida, Ayumu,Tanigaki, Hiroaki,Inokuchi, Eriko,Sasaki, Yoshikazu,Oishi, Shinya,Ohno, Hiroaki,Tamamura, Hirokazu,Wang, Zixuan,Peiper, Stephen C.,Kitaura, Kazuo,Otaka, Akira,Fujii, Nobutaka
, p. 3942 - 3951 (2007/10/03)
Organocopper-mediated anti-SN2′ reactions of γ-phosphoryloxy-α,β-unsaturated-δ-lactams were used to prepare highly functionalized diketopiperazine mimetics. The substrate phosphates 24, 32, and 47 were prepared from a-amino acid-derived allylic
Synthesis of (Z)-alkene and (E)-fluoroalkene-containing diketopiperazine mimetics utilizing organocopper-mediated reduction-alkylation and diastereoselectivity examination using DFT calculations
Niida, Ayumu,Mizumoto, Makiko,Narumi, Tetsuo,Inokuchi, Eriko,Oishi, Shinya,Ohno, Hiroaki,Otaka, Akira,Kitaura, Kazuo,Fujii, Nobutaka
, p. 4118 - 4129 (2007/10/03)
We have carefully examined the organocopper-mediated reduction-alkylation of γ-acetoxy or γ,γ-difluoro-α,β-unsaturated- δ-lactams for the synthesis of (Z)-alkene- or (E)-fluoroalkene-containing diketopiperazine mimetics. Reduction of acetates 2, 12, 14, a
Facile access to (Z)-alkene-containing diketopiperazine mimetics utilizing organocopper-mediated anti-SN2′ reactions
Niida, Ayumu,Oishi, Shinya,Sasaki, Yoshikazu,Mizumoto, Makiko,Tamamura, Hirokazu,Fujii, Nobutaka,Otaka, Akira
, p. 4183 - 4186 (2007/10/03)
Regio- and stereoselective anti-SN2′ alkylation of γ-phosphoryloxy-α,β-unsaturated-δ-lactams with organocopper reagents allowing the preparation of N-alkylated-α,δ- substituted-β,γ-unsaturated-δ-lactams as highly functionalized diketopiperazine
A Thermodynamic Preference of Chiral N-Methanesulfonyl and N-Arenesulfonyl 2,3-cis-3-Alkyl-2-Vinylaziridines over Their 2,3-Trans-Isomers: Useful Palladium(0)-Catalyzed Equilibration Reactions for the Synthesis of (E)-Alkene Dipeptide Isosteres
Ibuka, Toshiro,Mimura, Norio,Aoyama, Hiroshi,Akaji, Masako,Ohno, Hiroaki,Miwa, Yoshihisa,Taga, Tooru,Nakai, Kazuo,Tamamura, Hirokazu,Fujii, Nobutaka,Yamamoto, Yoshinori
, p. 999 - 1015 (2007/10/03)
Palladium(0)-catalyzed reactions of N-methanesulfonyl- or N-(arenesulfonyl)-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations. A highly stereoselective synthetic route to (E)-alkene dipeptide isosteres having desired stereochemistries from 2,3-cis-3-isobutyl-2-vinylaziridine by the use of organocopper chemistry is also presented.
Design and synthesis of novel protease inhibitors. Tripeptide α′,ss′-epoxyketones as nanomolar inactivators of the proteasome
Spaltenstein, Andrew,Leban, Johann J.,Huang, Jim J.,Reinhardt, Kelli R.,Viveros, O. Humberto,Sigafoos, Jim,Crouch, Ronald
, p. 1343 - 1346 (2007/10/03)
Tripeptide α′,β′-epoxyketones were prepared stereospecifically starting from Boc-[S]-phenylalanine. Diastereomer 5b inhibited the chymotrypsin-like activity of porcine endothelial cell derived proteasome at low nanomolar concentrations.
Stereoselective vinylation of amino aldehydes using 2-trimethylsilylethylidentriphenylphosphorane
Franciotti,Mann,Taddei
, p. 6783 - 6786 (2007/10/02)
2-Trimethylsilylethylidentriphenylphosphorane reacts stereoselectively with α-amino aldehydes giving the Cram chelation controlled product of vinylation of the carbonyl group. The olefinic 1,2-amino alcohols obtained with this reaction are important inter
The "benzostabase" protecting group for primary amines; application to aliphatic amines
Bonar-Law,Davis,Dorgan,Reetz,Wehrsig
, p. 6725 - 6728 (2007/10/02)
The "benzostabase" (BSB) protecting group has been applied to primary aliphatic amines. It can be introduced via a dehydrogenative silylation employing an air- and moisture-stable reagent, and is appreciably more acid-stable than the related "stabase" group. BSB protection has been used in a stereoselective synthesis of amino-alcohols involving the addition of organometallic reagents to protected amino-aldehydes under "non-chelation control".
