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Literature DB >> 15727477

Extending Pummerer reaction chemistry. Synthesis of (+/-)-dibromophakellstatin by oxidative cyclization of an imidazole derivative.

Abstract

The diastereoselective oxidative cyclization of a dihydrooroidin derivative is reported. The thioimidate product formed by application of a new variant of the Pummerer reaction serves as a precursor to dibromophakellstatin. [reaction: see text]

Entities: Chemical

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Year: 2005 PMID： 15727477 DOI： 10.1021/ol0500113

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

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Cited

12 in total

1. Palau'amine and related oroidin alkaloids dibromophakellin and dibromophakellstatin inhibit the human 20S proteasome.

Authors: Theresa A Lansdell; Nicole M Hewlett; Amanda P Skoumbourdis; Matthew D Fodor; Ian B Seiple; Shun Su; Phil S Baran; Ken S Feldman; Jetze J Tepe
Journal: J Nat Prod Date: 2012-05-16 Impact factor: 4.050

2. Palladium-catalyzed direct functionalization of imidazolinone: synthesis of dibromophakellstatin.

Authors: Jianming Lu; Xianghui Tan; Chuo Chen
Journal: J Am Chem Soc Date: 2007-06-01 Impact factor: 15.419

3. Synthetic access to the chlorocyclopentane cores of the proposed original and revised structures of palau'amine.

Authors: Michael S Bultman; Jun Ma; David Y Gin
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

4. Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors: Yuyong Ma; Saptarshi De; Chuo Chen
Journal: Tetrahedron Date: 2015-02-25 Impact factor: 2.457

Review 5. 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

Extending Pummerer reaction chemistry. Synthesis of (+/-)-dibromophakellstatin by oxidative cyclization of an imidazole derivative.

1. Palau'amine and related oroidin alkaloids dibromophakellin and dibromophakellstatin inhibit the human 20S proteasome.

2. Palladium-catalyzed direct functionalization of imidazolinone: synthesis of dibromophakellstatin.

3. Synthetic access to the chlorocyclopentane cores of the proposed original and revised structures of palau'amine.

4. Syntheses of Cyclic Guanidine-Containing Natural Products.

Review 5. Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

6. Total synthesis of the natural product (±)-dibromophakellin and analogues.

7. Revisiting the Kinnel-Scheuer hypothesis for the biosynthesis of palau'amine.

Review 8. Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses.

9. Sulfoxide-Directed Metal-Free ortho-Propargylation of Aromatics and Heteroaromatics.

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