118916-87-3Relevant academic research and scientific papers
Tin(ii) chloride assisted synthesis of N-protected γ-amino β-keto esters through semipinacol rearrangement
Bandyopadhyay, Anupam,Agrawal, Neha,Mali, Sachitanand M.,Jadhav, Sandip V.,Gopi, Hosahudya N.
experimental part, p. 4855 - 4860 (2010/12/24)
A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(ii) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction is mild, instantaneous and compatible with Boc-, Fmoc- and Cbz-amino protecting groups.
Stereochemistry and total synthesis of janolusimide, a tripeptide marine toxin
Giordano, Assunta,Della Monica, Carmela,Landi, Francesco,Spinella, Aldo,Sodano, Guido
, p. 3979 - 3982 (2007/10/03)
The stereochemistry of janolusimide, a lipophilic tripeptide marine toxin, has been fully elucidated by stereoselective synthesis of the lactam component (5S)-3,3'-dimethyl-5-isopropylpyrrolidin-2,4-dione. The peptide was then synthesized in 13 steps and in 0.8% total yield. (C) 2000 Elsevier Science Ltd.
Enantioselective and diastereoselective formation of syn-3-hydroxy-4-amino acids (syn-statines) via tetramic acids
Schmidt,Riedl,Haas,Griesser,Vetter,Weinbrenner
, p. 216 - 220 (2007/10/02)
Enantiomerically pure pyrrolidine-2,4-diones (tetramic acids) which can be diastereoselectively hydrogenated to syn-statines (4-amino-3-hydroxy-6-methylheptanoic acids) have been prepared by catalytic hydrogenation of 4-(benzyloxycarbonylamino)-3-oxocarboxylic acid esters.
AN IMPROVED SYNTHESIS OF β-KETO ESTER UNITS IN DIDEMNINS, USING 2,2'-CARBONYL-BIS(3,5-DIOXO-4-METHYL-1,2,4-OXADIAZOLIDINE).
Jouin, Patrick,Poncet, Joel,Dufour, Marie-Noelle,Maugras, Isabelle,Pantaloni, Antoine,Castro, Bertrand
, p. 2661 - 2664 (2007/10/02)
Activation of N-protected α-amino acids and O-protected α-hydroxy acids with 2,2'-carbonyl-bis(3,5-dioxo-4-methyl-1,2,4-oxadiazolidine) 6 provide a stable activated intermediate 7 suitable for the synthesis of β-keto ester 8.This activation was used in th
