110562-20-4

Upstream product

• 71461-30-8 (S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester 
• 149-73-5 trimethyl orthoformate 
• 6216-63-3 N-Cbz-Prolinol 
• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 

Downstream Products

• 80279-24-9 tilivalline 
• 110562-23-7 O-benzyltilivalline 
• 110575-89-8 (2-Amino-3-benzyloxy-phenyl)-((S)-2-dimethoxymethyl-pyrrolidin-1-yl)-methanone 
• 110562-21-5 N-(-3-methoxy-2-aminobenzoyl)-L-prolinal dimethyl acetal 
• 110562-22-6 (2-Amino-3-hydroxy-phenyl)-((S)-2-dimethoxymethyl-pyrrolidin-1-yl)-methanone 
• 260391-72-8 [2-((S)-2-Dimethoxymethyl-pyrrolidine-1-carbonyl)-4,5-dimethoxy-phenyl]-carbamic acid 2-benzenesulfonyl-ethyl ester 
• 260391-48-8 7,8,11-trimethoxy-5-oxo-2,3,11,11a-tetrahydro-1H,5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carboxylic acid 2-phenylsulfanyl-ethyl ester 
• 260391-70-6 ((S)-2-Dimethoxymethyl-pyrrolidin-1-yl)-(4,5-dimethoxy-2-nitro-phenyl)-methanone 
• 260391-71-7 (2-Amino-4,5-dimethoxy-phenyl)-((S)-2-dimethoxymethyl-pyrrolidin-1-yl)-methanone 

Relevant academic research and scientific papers

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.

Synthesis and biological evaluation of an N10-Psec substituted pyrrolo[2,1-c][1,4]benzodiazepine prodrug

The first example of an N10-protected (e.g., Psec, 15) pyrrolo[2,1-c][1,4]benzodiazepine (PBD) analogue that retains significant cytotoxicity in a number of tumour cell lines is reported. This prototype could lead to a new generation of clinically useful N10-protected PBD prodrugs.