Cascade Reactions. A Simple One??pot Synthesis of the Mitomycin Skeleton

…, G Geffroy, D Le Nouen, D Spileers…

Index: Defoin; Geffroy; Le Nouen; Spileers; Streith Helvetica Chimica Acta, 1989 , vol. 72, # 6 p. 1199 - 1215

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Citation Number: 14

Abstract

Abstract Nitroso-arene dienophiles 1 react regiospecifically with the conjugated dienals 2 and 3a/3b, and lead thereby to the unstable Diels-Alder cycloadducts 4 and 5. These undergo two types of cascade reactions which give pyridinium betaines 6 and pyrrolo- indoles 8 as the major reaction products. The one-pot syntheses of pyrroloindoles 8 represent a new and easy access to the basic skeleton of mitomycins 10. The scope and ...