112373-38-3

Upstream product

• 112373-16-7 4,5-diiodo-3-methoxy-2-(methoxycarbonyl)pyrrole 
• 112373-17-8 3-methoxy-2-(methoxycarbonyl)pyrrole 
• 112373-19-0 4-methoxy-5-(methoxycarbonyl)-1,1'-carbonyl-2,2'-bipyrrole 
• 112373-18-9 3-methoxy-2-(methoxycarbonyl)-1,1'-carbonyldipyrrole 
• 112373-36-1 4-methoxy-5-(methoxycarbonyl)-2,2'-bipyrrole 
• 325460-96-6 4-methoxy-1H,1'H-[2,2']bipyrrolyl-5-carboxylic acid tert-butyl ester 
• 182818-88-8 3-methoxypyrrole-2-carboxylic acid tert-butyl ester 
• 112373-37-2 4-Methoxy-1H,1'H-[2,2']bipyrrolyl-5-carboxylic acid hydrazide 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 10476-41-2 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde 
• 82-89-3 4-methoxy-5-[(Z)-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-1H,1'H-2,2'-bipyrrole 
• 52340-48-4 undecylprodigiosin 

Relevant academic research and scientific papers

Pyrrole-singlet oxygen reactions leading to α,α'-bipyrroles. Synthesis of prodigiosin and analogs

Reaction of the tert-butyl ester of 3-methoxy-2-pyrrolecarboxylic acid with singlet oxygen yields a hydroperoxide intermediate which undergoes coupling with pyrroles to yield precursors of prodigiosin and ring A analogs, readily convertible to the corresponding tripyrromethenes.

Total Synthesis of Prodigiosin, Prodigiosene, and Desmethoxyprodigiosin: Diels-Adler Reactions of Heterocyclic Azadienes and Development of an Effective Palladium(II)-Promoted 2,2'-Bipyrrole Coupling Procedure

The total synthesis of prodigiosin (1), a red pigment first isolated from Serratia marcescens, possessing the characteristic pyrrolylpyrromethene skeleton of a class of naturally occurring polypyrroles exhibiting antimicrobial and cytotoxic properties, is detailed.The approach is based application of an inverse electron demand Diels-Adler reaction of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate in a 1,2,4,5-tetrazine--->1,2-diazine--->pyrrole strategy for preparation of prodigiosin pyrrole ring B and the subsequent implementation of an effective intramolecular palladium(II)-promoted 2,2'-diaryl coupling for construction of the prodigiosin 2,2'-bipyrrole AB ring system.In situ generated activated ester derivatives of pyrrole-1-carboxylic acid or the use of pyrrole-1-carboxylic acid anhydride proved suitable for the generation of mixed 1,1'-carbonyldipyrrole compounds for use in the palladium(II)-promoted mixed, 2,2'-bipyrrole coupling.Extensions of this approach to the preparation of the naturally occurring parent pyrrolylpyrromethene, prodigiosene (2a), and 2-methyl-3-pentylprodigiosene (2e, desmethoxyprodigiosin) are detailed.A comparison of the in vitro cytotoxic properties of prodigiosin (1), prodigiosene (2a), and 2-methyl-3-pentylprodigiosene (2e) are reported and reveal exceptional cytotoxic potency (3.7*10-4 μg/mL = 3.7*10-10 g/mL) for prodigiosin against 9PS (P388) mouse leukemia which may be attributed to the presence of the prodigiosin C-6 methoxy substituent.

TOTAL SYNTHESIS OF PRODIGIOSIN

The total synthesis of prodigiosin (1), possessing the characteristic pyrrolylpyrromethene skeleton of a class of naturally-occuring polypyrroles, is detailed.The approach is based on the application of an inverse electron demand Diels-Alder reaction of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate in a 1,2,4,5-tetrazine -> 1,2-diazine -> pyrrole strategy for preparation of prodigiosin pyrrole ring B and the subsequent implementation of an intramolecular palladium(II)-promoted 2,2'-diaryl (2,2'-bipyrrole) coupling for construction of the prodigiosin 2,2'-bipyrrole AB ring system.