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Cascade Reactions. A Simple One‐pot Synthesis of the Mitomycin Skeleton
Author(s) -
Defoin Albert,
Geffroy Guillaume,
Le Nouen Didier,
Spileers Didier,
Streith Jacques
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720604
Subject(s) - chemistry , cascade , pyridinium , cascade reaction , skeleton (computer programming) , conjugated system , scope (computer science) , combinatorial chemistry , nitroso , stereochemistry , organic chemistry , catalysis , polymer , chromatography , computer science , programming language
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 limitations of the cascade reactions were investigated.