A Highly Stereoselective Synthesis of the Functionalized (E)-Alkene Dipeptide Isostere of Trp-Val via Organocyanocopper-Lewis Acid Mediated Reaction.
M Noda, T Ibuka, H Habashita, N FUJII
Index: Noda, Masaki; Ibuka, Toshiro; Habashita, Hiromu; Fujii, Nobutaka Chemical and Pharmaceutical Bulletin, 1997 , vol. 45, # 8 p. 1259 - 1264
Full Text: HTML
Citation Number: 9
Abstract
A stereocontrolled synthesis of the (E)-alkene dipeptide isostere of Trp-Val is described. The stereospecific α-alkylation of the δ-amino-γ-mesyloxy-α, β-unsaturated ester via the organocyanocopper-Lewis acid mediated reaction, based on 1, 3-transfer of chirality, was successfully applied for the key step in the synthetic sequence.
Related Articles:
Synthesis of new chiral peptide nucleic acid (PNA) monomers
[Falkiewicz; Wisniowski; Kolodziejczyk; Wisniewski Nucleosides, Nucleotides and Nucleic Acids, 2001 , vol. 20, # 4-7 p. 1393 - 1397]
[Ciapetti, Paola; Taddei, Maurizio; Ulivi, Paola Tetrahedron Letters, 1994 , vol. 35, # 19 p. 3183 - 3186]