183890-46-2

Upstream product

• 114340-53-3 2-tert-butyl-1,3-di-N-(hydroxyl) succinimidyl citrate 
• 97347-42-7 (+)-(S)-N₂,N₆-bis[(1,1-dimethylethoxy)carbonyl]-6-oxo-lysine methyl ester 
• 1025782-34-6 6-hydroxypiperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 183890-42-8 (S)-2-tert-Butoxycarbonylamino-6-[[(E)-(3-phenyl-acryloyl)]-(2-trimethylsilanyl-ethoxy)-amino]-hexanoic acid methyl ester 
• 183890-38-2 methyl (2S)-N-tert-butoxycarbonyl-6-oxopiperidine-2-carboxylate 
• 158414-69-8 (-)-(S)-6-oxo-2-piperidinecarboxylic acid methyl ester 
• 183890-50-8 (S)-6-tert-Butoxycarbonylamino-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 

Downstream Products

• 133705-25-6 nannochelin A 
• 183890-47-3 (S)-2-(3-Carboxy-3-hydroxy-4-{(S)-1-methoxycarbonyl-5-[[(E)-(3-phenyl-acryloyl)]-(2-trimethylsilanyl-ethoxy)-amino]-pentylcarbamoyl}-butyrylamino)-6-[[(E)-(3-phenyl-acryloyl)]-(2-trimethylsilanyl-ethoxy)-amino]-hexanoic acid methyl ester 

Relevant academic research and scientific papers

A total synthesis of nannochelin A. A short route to optically active Nω-hydroxy-α-amino acid derivatives

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.