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Literature DB >> 12076147

Synthesis of axinohydantoins.

Ana Carolina Barrios Sosa¹, Kenichi Yakushijin, David A Horne.

Abstract

A short synthesis of the hydantoin-containing marine sponge metabolites axinohydantoins is described. A key feature of the synthesis is a putative biomimetic, intramolecular cyclization of alpha-functionalized imidazolone 5, which affords the tricyclic pyrroloazepinone framework comprising 6. In addition, the conversion of imidazolones to alpha,beta-unsaturated hydantoins is outlined and represents a new approach to these heterocyclic systems.

Entities: Chemical Disease

Mesh：

Substances：
Hydantoins
Pyrroles

Year: 2002 PMID： 12076147 DOI： 10.1021/jo020063v

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

Keyword Cloud
Cited

15 in total

1. Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.

Authors: Ian B Seiple; Shun Su; Ian S Young; Akifumi Nakamura; Junichiro Yamaguchi; Lars Jørgensen; Rodrigo A Rodriguez; Daniel P O'Malley; Tanja Gaich; Matthias Köck; Phil S Baran
Journal: J Am Chem Soc Date: 2011-08-23 Impact factor: 15.419

2. A tandem synthesis of 5-sulfonylimino-2-imidazolones from sulfonoketenimides and dialkyl azodicarboxylates.

Authors: Issa Yavari; Manijeh Nematpour; Ehsan Ghanbari
Journal: Mol Divers Date: 2014-06-13 Impact factor: 2.943

Review 3. Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

Authors: Ali Al-Mourabit; Manuel A Zancanella; Supriya Tilvi; Daniel Romo
Journal: Nat Prod Rep Date: 2011-05-09 Impact factor: 13.423

Synthesis of axinohydantoins.

1. Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.

2. A tandem synthesis of 5-sulfonylimino-2-imidazolones from sulfonoketenimides and dialkyl azodicarboxylates.

Review 3. Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

4. Fluorous synthesis of hydantoins and thiohydantoins.

5. Methyl (1H-pyrrol-2-ylcarbonyl-amino)acetate.

6. 3-(1-Ethyl-1H-pyrrole-2-carboxamido)propionic acid monohydrate.

7. 1-Ethyl-1H,6H-pyrrolo[2,3-c]azepine-4,8(5H,7H)-dione.

8. 1H-Pyrrole-2-carboxylic acid.

9. Cu(I)-catalyzed C-H alpha-amination of aryl ketones: direct synthesis of imidazolinones.

Review 10. A submarine journey: the pyrrole-imidazole alkaloids.