110562-23-7

Upstream product

• 120-72-9 indole 
• 110575-89-8 (2-Amino-3-benzyloxy-phenyl)-((S)-2-dimethoxymethyl-pyrrolidin-1-yl)-methanone 
• 61535-24-8 2-amino-3-(benzyloxy)benzoic acid 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 69610-41-9 Boc-L-Pro-H 
• 110562-19-1 tert-butoxycarbonyl-L-prolinal dimethyl acetal 
• 71461-30-8 (S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester 
• 110562-20-4 Cbz-Pro-L-prolinal dimethyl acetal 

Downstream Products

• 80279-24-9 tilivalline 

Relevant academic research and scientific papers

New methods and reagents in organic synthesis. 92. A stereoselective synthesis of tilivalline and its analogs

Tilivalline (1a), a metabolite from Klebsiella pneumoniae var. oxytoca, and its derivatives 1 have been efficiently and stereoselectively synthesized from diphenyl phosphorazidate, the 2-oxazoline 2, the L-proline derivatives 5, and indole; the key step is a Mannich type intramolecular cyclization accompanied with completely stereoselective introduction of indole. Furthermore, 11-substituted 5H- pyrrolo[2,1-c][1,4]benzodiazepin-5-ones (16) have been also synthesized from the acetal amide 9a and various nucleophiles by the use of this new Mannich type cyclization.

NEW METHOD AND REAGENTS IN ORGANIC SYNTHESIS. 65. A STEREOSELECTIVE SYNTHESIS OF TILIVALLINE

Tilivalline (1), a metabolite from Klebsiella, has been efficiently and stereoselectively synthesized from diphenyl phosphorazidate (DPPA), the 2-oxazoline 2, the L-proline derivative 5, and indole; the key step is a Mannich type intramolecular cyclization accompanied with simultaneous and completely stereoselective introduction of indole.