92144-07-5Relevant academic research and scientific papers
TOTAL SYNTHESIS OF PRODIGIOSIN
Boger, Dale L.,Patel, Mona
, p. 2499 - 2502 (1987)
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.
Synthesis of isochrysohermidin - Distamycin hybrids
Yeung, Bryan K. S.,Boger, Dale L.
, p. 5249 - 5253 (2003)
The synthesis of the alkylating subunit of the DNA cross-linking agent, isochrysohermidin (2), and its subsequent incorporation into conjugates with distamycin A (1) are described. The DNA binding properties of these agents were compared to that of distamycin A, using a fluorescence intercalator displacement (FID) assay.
Silyl enol ethers as 2π components in (4+2) cycloadditions: Preparative and kinetic results
Hierstetter,Tischler,Sauer
, p. 8019 - 8022 (1992)
Easily accessible open chain and cyclic silyl enolethers show dienophilic reactivity in (4+2)-cycloaddition reactions with inverse electron demand equivalent to enol ethers. Preparative and kinetic results are reported.
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
Boger, Dale L.,Patel, Mona
, p. 1405 - 1415 (2007/10/02)
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.
Thermal Cycloaddition of Dimethyl 1,2,4,5-Tetrazine-3,6-dicarboxylate with Electron-Rich Olefins: 1,2-Diazine and Pyrrole Introduction. Preparation of Octamethylporphin (OMP)
Boger, Dale L.,Coleman, Robert S.,Panek, James S.,Yohannes, Daniel
, p. 4405 - 4409 (2007/10/02)
An investigation of the inverse electron demand Diels-Alder reactions of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with electron-rich olefins for the introduction of 1,2-diazines and pyrroles is described.A short synthesis of 2,3,7,8,12,13,17,18-octamethylporphin (OMP) is detailed.
