93200-02-3Relevant academic research and scientific papers
ASYMMETRIC HYDROGENATION OF N-(α-KETOACYL)-α-AMINO ESTERS
Tani, Kazuhide,Tanigawa, Eiji,Tatsuno, Yoshitaka,Otsuka, Sei
, p. 737 - 738 (1986)
Asymmetric hydrogenation of N-(α-ketoacyl)-α-amino esters with Cydiop-rhodium(I) complex catalysts produced optically active N-(α-hydroxyacyl)-α-amino esters in high optical yields, which may be useful as building blocks of depsipeptides.Almost no influen
Shornephine A: Structure, chemical stability, and P-glycoprotein inhibitory properties of a rare diketomorpholine from an Australian marine-derived Aspergillus sp.
Khalil, Zeinab G.,Huang, Xiao-Cong,Raju, Ritesh,Piggott, Andrew M.,Capon, Robert J.
, p. 8700 - 8705 (2014/12/12)
Chemical analysis of an Australian marine sediment-derived Aspergillus sp. (CMB-M081F) yielded the new diketomorpholine (DKM) shornephine A (1)together with two known and one new diketopiperazine (DKP), 15b-β-hydroxy-5-N-acetyladreemin (2), 5-N-acetyladreemin (3), and 15b-β-methoxy-5-N-acetyladreemin (4), respectively. Structure elucidation of 1.4 was achieved by detailed spectroscopic analysis, supported by chemical degradation and derivatization, and biosynthetic considerations. The DKM (1)underwent a facile (auto) acid-mediated methanolysis to yield seco-shornephine A methyl ester (1a). Our mechanistic explanation of this transformation prompted us to demonstrate that the acid-labile and solvolytically unstable DKM scaffold can be stabilized by N-alkylation. Furthermore, we demonstrate that at 20 μM shornephine A (1)is a noncytotoxic inhibitor of P-glycoprotein-mediated drug efflux in multidrug-resistant human colon cancer cells.
Synthesis of chiral depsipeptide building block via asymmetric hydrosilylation
Yao, Jin-Shui,Wu, You-Shi
, p. 553 - 556 (2007/10/03)
Asymmetric hydrosilylation of N-(α-ketoacyl)-α-amino esters was performed, catalyzed by rhodium(I) complex of chiral 2-(2-pyridyl)-4-carbomethoxy-1,3-thiazolidine or Rh(PPh3)3Cl. The N-(α-hydroxyacyl)-α-amino esters were synthesized
trans-1,3-Dithiane-1,3-Dioxide, a New Chiral Acyl Anion Equivalent for the Preparation of Masked Activated Acids: Application to the Synthesis of α-Hydroxy Acid Derivatives
Aggarwal, Varinder K.,Thomas, Abraham,Franklin, Richard J.
, p. 1653 - 1654 (2007/10/02)
trans-1,3-Dithiane-1,3-dioxide reacts with high diastereoselectivity with aromatic aldehydes and the 1,3-dithiane-1,3-dioxide moiety can be easily converted to a thiolester without racemisation by carrying out a Pummerer reaction; the thiolester is a group that can be readily transformed into acids, esters, amides, ketones and aldehydes.
Preparation of optically active peralkyldiphosphines and their use, as the rhodium(I) complex, in the asymmetric catalytic hydrogenation of ketones
Tani, Kazuhide,Suwa, Kenichi,Tanigawa, Eiji,Ise, Tomokazu,Yamagata, Tsuneaki,et al.
, p. 203 - 222 (2007/10/02)
Two types of the optically active peralkyldiphosphine, 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(dialkylphosphino)butane (Rdiop 3) and N-(N'-substituted carbamoyl)-4-dicyclohexylphosphino-2-dicyclohexylphosphinomethylpyrrolidine (R-Cycapp 8), have been p
SYNTHESIS OF CHIRAL OLIGOPEPTIDES BY MEANS OF CATALYTIC ASYMMETRIC HYDROGENATION OF DEHYDROPEPTIDES
Ojima, Iwao,Yoda, Noriko,Yatabe, Momoko,Tanaka, Toshiyuki,Kogure, Tetsuo
, p. 1255 - 1268 (2007/10/02)
Asymmetric hydrogenation of Ac-ΔTyr(Ac)-(S)-Ala-Gly-OMe (6), Ac-ΔTyr(Ac)-(R)-Ala-Gly-(S)-Phe-OMe (7), Ac-ΔPhe-NH-CH(R)-CH2-OCH2Ph (10), HCO-ΔPhe-(S)-Leu-OMe (16), X-AA-ΔPhe-AA'-OMe ( 5: X=tBOC, CBZ, CF3CO; AA, AA'= α-amino acid ), and t
SYNTHESIS OF CHIRAL DEPSIPEPTIDE BUILDING BLOCK BY THE ASYMMETRIC REDUCTION OF N-(α-KETOACYL)-α-AMINO ESTERS
Ojima, Iwao,Tanaka, Toshiyuki,Kogure, Tetsuo
, p. 823 - 826 (2007/10/02)
Asymmetric reduction of N-(α-ketoacyl)-α-amino esters was performed by using homogeneous hydrosilylation and hydrogenation catalyzed by rhodium(I) complexes.The asymmetric hydrosilylation achieved good to high stereoselectivities giving the corresponding
