92144-07-5Relevant articles and documents
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.
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.
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.