3519-30-0Relevant academic research and scientific papers
First total synthesis of neoantimycin
Ogawa, Hikaru,Iio, Hideo,Usuki, Yoshinosuke
, p. 1214 - 1216 (2015/09/22)
The first total synthesis of neoantimycin (1), an unusual ring-extended antibiotic of the antimycin class, has been achieved, using intramolecular transesterification for construction of the 15-membered tetralactone core.
Kinetic resolution of racemic α-tert-alkyl-α-hydroxy esters by enantiomer-selective carbamoylation
Kurono, Nobuhito,Ohtsuga, Kentaro,Wakabayashi, Masanori,Kondo, Tadahiro,Ooka, Hirohito,Ohkuma, Takeshi
experimental part, p. 10312 - 10318 (2012/01/30)
Kinetic resolution of sterically hindered racemic α-tert-alkyl- α-hydroxy esters is performed by enantiomer-selective carbamoylation with the t-Bu-Box-Cu(II) catalyst (Box = bis-(oxazoline)). The reaction with 0.5 equiv of n-C3H7NCO is carried out with a substrate-to-catalyst molar ratio of 500-5000 at -20 to 25 °C. The high enantiomer-discrimination ability of the catalyst achieves an excellent stereoselectivity factor (s = kfast/kslow) of 261 in the best case. A catalytic cycle for this reaction is proposed (Figure presented).
Zinc-catalyzed enantiospecific sp3-sp3 cross-coupling of α-hydroxy ester triflates with grignard reagents
Studte, Christopher,Breit, Bernhard
supporting information; experimental part, p. 5451 - 5455 (2009/03/12)
(Chemical Equation Presented) Zinc chloride does the trick and efficiently catalyzes the enantiospecific cross-coupling of α-hydroxy ester triflates with Grignard reagents under mild conditions. Enantiopure α-hydroxy esters are directly available from the chiral pool or by diazotization of α-amino acids. Substantial variations in both reacting partners are tolerated making this methodology an attractive alternative to enolate alkylation featuring a reversal of polarity.
Amber force field implementation, molecular modelling study, synthesis and MMP-1/MMP-2 inhibition profile of (R)- and (S)-N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)-3-methylbutanamides
Tuccinardi, Tiziano,Martinelli, Adriano,Nuti, Elisa,Carelli, Paolo,Balzano, Federica,Uccello-Barretta, Gloria,Murphy, Gillian,Rossello, Armando
, p. 4260 - 4276 (2007/10/03)
Ab initio calculations (B3LYP/Lanl2DZ level of theory) were performed in this study to determine all the structural and catalytic zinc parameters required in order to study MMPs and their complexes with hydroxamate inhibitors by means of the AMBER force f
N-i-Propoxy-N-biphenylsulfonylaminobutylhydroxamic acids as potent and selective inhibitors of MMP-2 and MT1-MMP
Rossello, Armando,Nuti, Elisa,Carelli, Paolo,Orlandini, Elisabetta,Macchia, Marco,Nencetti, Susanna,Zandomeneghi, Maurizio,Balzano, Federica,Barretta, Gloria Uccello,Albini, Adriana,Benelli, Roberto,Cercignani, Giovanni,Murphy, Gillian,Balsamo, Aldo
, p. 1321 - 1326 (2007/10/03)
Structural manipulation of the pharmacophoric model of type A selective MMP inhibitors (MMPi), obtained by the insertion of some alkyl substituents R 2 possessing an appropriate geometry, steric bulkiness and lipophilicity, is able to improve p
Synthesis and characterization of chiral N-O turns induced by α-aminoxy acids
Yang,Li,Ng,Yan,Qu,Wu
, p. 7303 - 7312 (2007/10/03)
Chiral α-aminoxy acids of various side chains were synthesized with high optical purity starting from chiral α-amino acids. The conformations of diamides 13a-e, 15, and 16 were probed by using NMR, FT-IR, and CD spectroscopic methods as well as X-ray crystallography. The right-handed turns with eight-membered-ring intramolecular hydrogen bonds between adjacent residues (called the N-O turns) were found to be preferred for D-aminoxy acid residues, and they were independent of the side chains. The rigid chiral N-O turns should have great potential in molecular design.
