Literature DB >> 17850163

Extending Pummerer reaction chemistry. Synthesis studies in the phakellin alkaloid area.

Ken S Feldman1, Amanda P Skoumbourdis, Matthew D Fodor.   

Abstract

The syntheses of (+/-)-dibromophakellstatin and, from this species, (+/-)-dibromophakellin are described. Oxidative cyclization of a phenylthiolated dihydrooroidin derivative triggered by a Pummerer reaction constitutes the key step in this biomimetic approach to this family of marine alkaloids.

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Year:  2007        PMID： 17850163     DOI： 10.1021/jo701487j

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


  5 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.  Total Synthesis of (±)-Dragmacidin E: Problems Solved and Lessons Learned.

Authors:  Ken S Feldman; Paiboon Ngernmeesri
Journal:  Synlett       Date:  2012-08       Impact factor: 2.454

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

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

Authors:  Nicole M Hewlett; Jetze J Tepe
Journal:  Org Lett       Date:  2011-07-28       Impact factor: 6.005

Review 5.  A submarine journey: the pyrrole-imidazole alkaloids.

Authors:  Barbara Forte; Beatrice Malgesini; Claudia Piutti; Francesca Quartieri; Alessandra Scolaro; Gianluca Papeo
Journal:  Mar Drugs       Date:  2009-11-27       Impact factor: 5.118
  5 in total

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