214277-31-3

Upstream product

• 125299-56-1 (11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-10-(benzyloxycarbonyl)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione 
• 24736-82-1 diethyl 3-hydroxyphthalate 
• 100-39-0 benzyl bromide 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 125299-61-8 8-(benzyloxy)-2H-benzo[d][1,3]oxazine-2,4(1H)-dione 
• 63382-37-6 4-(benzyloxy)isobenzofuran-1,3-dione 
• 501-53-1 benzyl chloroformate 
• 125326-16-1 (+)-(11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione 

Downstream Products

• 80279-24-9 tilivalline 
• 125299-55-0 (+)-(11S,11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-10-carbobenzyloxy-11-(3'-indolyl)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5-one 

Relevant academic research and scientific papers

Biosynthesis of the Enterotoxic Pyrrolobenzodiazepine Natural Product Tilivalline

The nonribosomal enterotoxin tilivalline was the first naturally occurring pyrrolobenzodiazepine to be linked to disease in the human intestine. Since the producing organism Klebsiella oxytoca is part of the intestinal microbiota and the pyrrolobenzodiaze

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.