125299-54-9

Upstream product

• 120-72-9 indole 
• 214277-12-0 (+)-(11aS)-1,2,3,10,11,11a-hexahydro-10-(benzyloxycarbonyl)-11-hydroxy-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5-one 
• 24919-40-2 (S)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione 
• 125299-58-3 (+)-(11aS)-1,2,3,10,11,11a-hexahydro-10-(benzyloxycarbonyl)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione 
• 501-53-1 benzyl chloroformate 
• 125299-59-4 (S)-11-Hydroxy-5-oxo-2,3,11,11a-tetrahydro-1H,5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Stereoselective synthesis of tilivalline

Tilivalline 1, a metabolite from Klebsiella pneumoniae var. ocytoca, was easily synthesized in five steps from (S)-proline and 3-(benzyloxy)isatoic anhydride 4g. This synthesis is based on modified Curtius reactions of 3- substituted phthalic anhydrides 11 to 3-substituted isatoic anhydrides 4, conversion of lactams 6 to the acyliminium precursors 7 and stereoselective introduction of indole from the less hindered side of 7.

STEREOSELECTIVE SYNTHESIS OF TILIVALLINE

Tilivalline (1b) was easily synthesized by converting lactam 3b to the acyliminium precursor 5b followed by stereoselectively introducing indole from the less hindered side of 5b.