Literature DB >> 21797255

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

Nicole M Hewlett1, Jetze J Tepe.   

Abstract

(±)-Dibromophakellin has been synthesized in two steps from a known alkene intermediate. The key step in the synthesis is the NBS olefin activation to facilitate the addition of a guanidine molecule across the double bond.

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Year:  2011        PMID： 21797255      PMCID： PMC3162990          DOI： 10.1021/ol201741r

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


  16 in total

1.  Total synthesis of the marine natural product rac-dibromophakellstatin.

Authors:  Delphine E N Jacquot; Michael Zöllinger; Thomas Lindel
Journal:  Angew Chem Int Ed Engl       Date:  2005-04-08       Impact factor: 15.336

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.  Enantioselective synthesis of (+)-monobromophakellin and (+)-phakellin: a concise phakellin annulation strategy applicable to Palau'amine.

Authors:  Shaohui Wang; Daniel Romo
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

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

Authors:  Ken S Feldman; Amanda P Skoumbourdis
Journal:  Org Lett       Date:  2005-03-03       Impact factor: 6.005

5.  Versatile access to C-4-substituted 2-amino-1,3-azoles from hydropyridines in oxidative conditions.

Authors:  Maria del Rayo Sanchez Salvatori; Robert Abou-Jneid; Saïd Ghoulami; Marie-Thérèse Martin; Anne Zaparucha; Ali Al-Mourabit
Journal:  J Org Chem       Date:  2005-09-30       Impact factor: 4.354

6.  Total synthesis of the cytostatic marine natural product dibromophakellstatin via three-component imidazolidinone anellation.

Authors:  Michael Zöllinger; Peter Mayer; Thomas Lindel
Journal:  J Org Chem       Date:  2006-12-08       Impact factor: 4.354

7.  Antitumor activity of the marine natural product dibromophakellstatin in vitro.

Authors:  Michael Zöllinger; Gerhard Kelter; Heinz-Herbert Fiebig; Thomas Lindel
Journal:  Bioorg Med Chem Lett       Date:  2006-10-24       Impact factor: 2.823

8.  Enantioselective total synthesis of (+)-dibromophakellstatin.

Authors:  Karine G Poullennec; Daniel Romo
Journal:  J Am Chem Soc       Date:  2003-05-28       Impact factor: 15.419

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

Authors:  Ken S Feldman; Amanda P Skoumbourdis; Matthew D Fodor
Journal:  J Org Chem       Date:  2007-09-13       Impact factor: 4.354

10.  Total synthesis of palau'amine.

Authors:  Ian B Seiple; Shun Su; Ian S Young; Chad A Lewis; Junichiro Yamaguchi; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2010-02-01       Impact factor: 15.336
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  9 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.  Generation and Reactivity of 2-Amido-1,3-diaminoallyl Cations: Cyclic Guanidine Annulations via Net (3 + 2) and (4 + 3) Cycloadditions.

Authors:  V Raghavendra Rao Kovvuri; Haoran Xue; Daniel Romo
Journal:  Org Lett       Date:  2020-02-03       Impact factor: 6.005

3.  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 4.  Applications of Friedel-Crafts reactions in total synthesis of natural products.

Authors:  Majid M Heravi; Vahideh Zadsirjan; Pegah Saedi; Tayebeh Momeni
Journal:  RSC Adv       Date:  2018-12-03       Impact factor: 4.036

5.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

Review 6.  Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses.

Authors:  Xiao Wang; Zhiqiang Ma; Xiaolei Wang; Saptarshi De; Yuyong Ma; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2014-05-15       Impact factor: 6.222

7.  Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products.

Authors:  Sultan Taskaya; Nurettin Menges; Metin Balci
Journal:  Beilstein J Org Chem       Date:  2015-05-28       Impact factor: 2.883

8.  Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties.

Authors:  Işıl Yenice; Sinan Basceken; Metin Balci
Journal:  Beilstein J Org Chem       Date:  2017-05-04       Impact factor: 2.883

9.  Natural product scaffolds as inspiration for the design and synthesis of 20S human proteasome inhibitors.

Authors:  Grace E Hubbell; Jetze J Tepe
Journal:  RSC Chem Biol       Date:  2020-09-16
  9 in total

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