The Journal of Organic Chemistry

Total synthesis of prodigiosin, prodigiosene, and desmethoxyprodigiosin: Diels-Alder reactions of heterocyclic azadienes and development of an effective palladium (II …

DL Boger, M Patel

Index: Boger, Dale L.; Patel, Mona Journal of Organic Chemistry, 1988 , vol. 53, # 7 p. 1405 - 1415

Full Text: HTML

Citation Number: 192

Abstract

The total synthesis of prodigiosin (l), 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 on the application of an inverse electron demand Diels-Alder reaction of dimethyl 1, 2, 4, 5-tetrazine-3, 6-dicarboxylat. e in a 1, 2, 4, 5-tetrazine-1, 2-diazine-pyrrole strategy for ...