133705-25-6Relevant articles and documents
A total synthesis of nannochelin A. A short route to optically active Nω-hydroxy-α-amino acid derivatives
Sakamoto, Takeshi,Li, Hao,Kikugawa, Yasuo
, p. 8496 - 8499 (2007/10/03)
The total synthesis of nannochelin A, a lysine-basd cinnamoyl hydroxamate produced by Nannocystis exedens, is described. The key transformation involves construction of the Nε-cinnamoyl-Nε-hydroxy-L-lysine methyl ester fragment by partial reduction of the lactam carbonyl of 6 derived from L-lysine, oximation of this aldehyde equivalent compound 8 with O-[2-(trimethylsilyl)ethyl]hydroxylamine, and reduction of the oxime 10, followed by N-acylation prior to coupling with the external carbonyls of citric acid. This methodology will be applicable to synthesis of other hydroxamate-containing siderophores bearing hydrogenolyzable groups in the molecule.
Synthesis of the hydroxamate siderophore nannochelin A
Mulqueen, Gerard C.,Pattenden, Gerald,Whiting, Donald A.
, p. 9137 - 9142 (2007/10/02)
A total synthesis of nannochelin A, a novel cinnamoyl-hydroxamate siderophore produced by Nannocystis exedens, is described.