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Literature DB >> 17165926

Synthesis of an advanced intermediate en route to the mitomycin natural products.

Amie L Williams¹, Jayasree M Srinivasan, Jeffrey N Johnston.

Abstract

[Structure: see text] An advanced intermediate in our planned synthesis of mitomycin C has been acquired in nine steps from tert-butyl glyoxylate. The aziridinyl pyrrolidine and quinone subunits are coupled regioselectively to arrive at an enamine that is prepared for C10 homologation.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2006 PMID： 17165926 PMCID： PMC2533355 DOI： 10.1021/ol0624676

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

14 in total

1. Formation of 9,10-unsaturation in the mitomycins: facile fragmentation of beta-alkyl-beta-aryl-alpha-oxo-gamma-butyrolactones.

Authors: F E Ziegler; M Y Berlin; K Lee; A R Looker
Journal: Org Lett Date: 2000-11-16 Impact factor: 6.005

2. Utility of the tandem Pauson-Khand reaction in the construction of tetracycles

Authors:
Journal: J Org Chem Date: 2000-04-07 Impact factor: 4.354

3. Oxazolium-derived azomethine ylides. External oxazole activation and internal dipole trapping in the synthesis of an aziridinomitosene.

Authors: E Vedejs; D W Piotrowski; F C Tucci
Journal: J Org Chem Date: 2000-09-08 Impact factor: 4.354

Review 4. Mitomycin C: small, fast and deadly (but very selective).

Authors: M Tomasz
Journal: Chem Biol Date: 1995-09

5. Aziridinomitosenes by anionic cyclization: deuterium as a removable blocking group.

Authors: Edwin Vedejs; Jeremy Little
Journal: J Am Chem Soc Date: 2002-02-06 Impact factor: 15.419

6. Unified synthesis of quinone sesquiterpenes based on a radical decarboxylation and quinone addition reaction.

Authors: Taotao Ling; Erwan Poupon; Erik J Rueden; Sun H Kim; Emmanuel A Theodorakis
Journal: J Am Chem Soc Date: 2002-10-16 Impact factor: 15.419

7. Synthesis of (-)-ilimaquinone via a radical decarboxylation and quinone addition reaction.

Authors: Taotao Ling; Erwan Poupon; Erik J Rueden; Emmanuel A Theodorakis
Journal: Org Lett Date: 2002-03-07 Impact factor: 6.005

8. Lobocyclamide B from Lyngbya confervoides. Configuration and asymmetric synthesis of beta-hydroxy-alpha-amino acids by (-)-sparteine-mediated aldol addition.

Authors: John B MacMillan; Tadeusz F Molinski
Journal: Org Lett Date: 2002-05-30 Impact factor: 6.005

9. Mitomycin synthetic studies: stereocontrolled and convergent synthesis of a fully elaborated aziridinomitosane.

Authors: Robert S Coleman; François-Xavier Felpin; Wei Chen
Journal: J Org Chem Date: 2004-10-15 Impact factor: 4.354

Review 10. Aziridines: epoxides' ugly cousins?

Authors: J B Sweeney
Journal: Chem Soc Rev Date: 2002-09 Impact factor: 54.564

5 in total

Review 1. Mitomycinoid alkaloids: mechanism of action, biosynthesis, total syntheses, and synthetic approaches.

Authors: Phillip D Bass; Daniel A Gubler; Ted C Judd; Robert M Williams
Journal: Chem Rev Date: 2013-05-08 Impact factor: 60.622

2. 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.

Authors: Jayasree M Srinivasan; Priya A Mathew; Amie L Williams; John C Huffman; Jeffrey N Johnston
Journal: Chem Commun (Camb) Date: 2011-02-24 Impact factor: 6.222