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Chem Commun (Camb) ; 47(13): 3975-7, 2011 Apr 07.
Article in English | MEDLINE | ID: mdl-21347494

ABSTRACT

A concise synthesis of a highly functionalized intermediate lacking only C10 of the mitomycin backbone is described. The key to this development is the Brønsted acid-catalyzed aza-Darzens reaction used to forge the cis-aziridine. Additionally an oxidative ketalization fortuitously occurs during the quinone-enamine coupling step, leading to an orthogonally protected hydroquinone.


Subject(s)
Antibiotics, Antineoplastic/chemical synthesis , Aziridines/chemical synthesis , Mitomycin/chemical synthesis , Antibiotics, Antineoplastic/chemistry , Aziridines/chemistry , Catalysis , Crystallography, X-Ray , Mitomycin/chemistry , Models, Molecular , Stereoisomerism
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