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Literature DB >> 21347494

Stereoselective synthesis of complex polycyclic aziridines: use of the Brønsted acid-catalyzed aza-Darzens reaction to prepare an orthogonally protected mitomycin C intermediate with maximal convergency.

Jayasree M Srinivasan¹, Priya A Mathew, Amie L Williams, John C Huffman, Jeffrey N Johnston.

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.

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Year: 2011 PMID： 21347494 PMCID： PMC3334326 DOI： 10.1039/c0cc05734g

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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References

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Stereoselective synthesis of complex polycyclic aziridines: use of the Brønsted acid-catalyzed aza-Darzens reaction to prepare an orthogonally protected mitomycin C intermediate with maximal convergency.

1. The role of mitomycin antibiotics in the chemotherapy of solid tumors.

2. The crystal and molecular structure of n-brosylmitomycin A.

3. The molecular structure of 7-demethoxy-7-p-bromoanilino mitomycin B.

Review 4. Mechanisms of action of quinone-containing alkylating agents. I: NQO1-directed drug development.

5. Catalytic Asymmetric Aziridination with Arylborate Catalysts Derived from VAPOL and VANOL Ligands This work was supported by the National Institutes of Health and was performed at the University of Chicago. VAPOL=2,2'-diphenyl-

Review 6. To protonate or alkylate? Stereoselective Brønsted acid catalysis of C-C bond formation using diazoalkanes.

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