152032-91-2

Upstream product

• 15865-57-3 2-nitro-3-methoxybenzoyl chloride 
• 1233705-47-9 (E)-3-[(S)-5-((tert-butyldimethylsilyloxy)methyl)-1-(3-methoxy-2-nitrobenzoyl)-4,5-dihydro-1H-pyrrol-3-yl]-N,N-dimethylacrylamide 
• 148680-22-2 Acetic acid (S)-4-formyl-1-(3-methoxy-2-nitro-benzoyl)-2,3-dihydro-1H-pyrrol-2-ylmethyl ester 
• 148680-21-1 Acetic acid (S)-1-(3-methoxy-2-nitro-benzoyl)-2,3-dihydro-1H-pyrrol-2-ylmethyl ester 
• 67040-46-4 (5S)-5-[(1-ethoxyethyl)oxymethyl]tetrahydro-1H-2-pyrrolone 
• 148680-23-3 Acetic acid (S)-4-((E)-2-dimethylcarbamoyl-vinyl)-1-(3-methoxy-2-nitro-benzoyl)-2,3-dihydro-1H-pyrrol-2-ylmethyl ester 

Downstream Products

• 110652-72-7 Porothramycin B 
• 152032-92-3 (E)-3-[(S)-5-Formyl-1-(3-methoxy-2-nitro-benzoyl)-4,5-dihydro-1H-pyrrol-3-yl]-N,N-dimethyl-acrylamide 

Relevant academic research and scientific papers

Concise formal synthesis of porothramycins A and B via zincke pyridinium ring-opening/ring-closing cascade

Short formal syntheses of the antitumor antibiotics porothramycins A and B from a commercially available ester of the unnatural amino acid 3-(3-pyridyl)alanine are presented. A rearrangement cascade that presumably involves a Zincke-type pyridinium ring-opening followed by cyclization of a pendant nucleophilic amide generates the salient pyrroline ring of the alkaloids.

Enantioselective synthesis of (+)porothramycin B and its 9-demethoxy analogue

(+)9-Demethoxyporothramycin B 3a and (+) porothramycin B 3b were synthesized from (S) pyroglutamic acid through a versatile and efficient route.