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Synthesis of granulatimide analogues bearing a maleimide instead of an imidazole heterocycle

โœ Scribed by Bernadette Hugon; Bruno Pfeiffer; Pierre Renard; Michelle Prudhomme

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
196 KB
Volume
44
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A synthesis in a few steps of a new family of granulatimide analogues was performed. In the new compounds, the aromatic framework of granulatimide is modified by replacement of the imidazole unit by a maleimide moiety. The synthesis of a water-soluble analogue is also presented.

๐Ÿ“œ SIMILAR VOLUMES

Synthesis of isogranulatimide analogues
Synthesis of isogranulatimide analogues possessing a pyrrole moiety instead of an imidazole heterocycle
โœ Bernadette Hugon; Bruno Pfeiffer; Pierre Renard; Michelle Prudhomme ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 224 KB

An efficient four step synthesis from commercial indoles of isogranulatimide analogues is reported. In the new compounds, the imidazole moiety is replaced by a pyrrole unit, the indole part is substituted or not in 5-position and the nitrogen of the imide moiety bears or not a methyl substituent.

Synthesis of isogranulatimides A and B a
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โœ Bernadette Hugon; Bruno Pfeiffer; Pierre Renard; Michelle Prudhomme ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 269 KB

The synthesis of a new family of isogranulatimides analogues is described in which a 7-azaindole replaces the indole moiety. The key step is the photocyclization of the aza didemnimide intermediates which leads to two isomeric analogues of isogranulatimides A and B. A derivative bearing a carbohydra