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Literature DB >> 15099080

Total synthesis of (+/-)-perophoramidine.

Abstract

The first total synthesis of racemic perophoramidine is described. The key step features the highly stereoselective introduction of the vicinial quaternary centers via base-promoted carbon-carbon bond formation between a 3-alkylindole and a 3-bromo-3-alkylindolin-2-one. This transformation presumably proceeds through a conjugate addition or Diels-Alder cycloaddition of the 3-alkylindole with a 3-alkylindol-2-one intermediate.

Entities: Chemical

Mesh：

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Year: 2004 PMID： 15099080 DOI： 10.1021/ja049569g

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

31 in total

1. Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

Authors: Timothy Newhouse; Chad A Lewis; Kyle J Eastman; Phil S Baran
Journal: J Am Chem Soc Date: 2010-05-26 Impact factor: 15.419

10. Protecting-group-free synthesis of 3-tert-prenylated oxindoles: contiguous all-carbon quaternary centers via tertiary neopentyl substitution.

Authors: Christopher D Grant; Michael J Krische
Journal: Org Lett Date: 2009-10-15 Impact factor: 6.005

Total synthesis of (+/-)-perophoramidine.

1. Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

2. Total Synthesis and Characterization of 7-Hypoquinuclidonium Tetrafluoroborate and 7-Hypoquinuclidone BF3 Complex.

Review 3. Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine.

4. Total synthesis of the polycyclic fungal metabolite (+/-)-communesin F.

5. Evolution of a strategy for total synthesis of the marine fungal alkaloid (+/-)-communesin F.

6. Convergent and Biomimetic Enantioselective Total Synthesis of (-)-Communesin F.

Review 7. Chemistry of bridged lactams and related heterocycles.

Review 8. Total Syntheses of Vancomycin-Related Glycopeptide Antibiotics and Key Analogues.

9. Interrupted Fischer indolization approach toward the communesin alkaloids and perophoramidine.

10. Protecting-group-free synthesis of 3-tert-prenylated oxindoles: contiguous all-carbon quaternary centers via tertiary neopentyl substitution.