Cascade Reactions. A Simple One‐pot Synthesis of the Mitomycin Skeleton | Zendy

Defoin Albert | Zendy; Geffroy Guillaume | Zendy; Le Nouen Didier | Zendy; Spileers Didier | Zendy; Streith Jacques | Zendy

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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.

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