Literature DB >> 17192109

Total synthesis of potential antitumor agent, (-)-dictyostatin.

P Veeraraghavan Ramachandran1, Amit Srivastava, Debasis Hazra.   

Abstract

[structure: see text] The potential antitumor agent (-)-dictyostatin has been synthesized utilizing Brown crotylboration to achieve eight of the eleven chiral centers. The yield for the 26-step longest sequence is approximately 4%. The C9-C10 coupling is achieved via a stereoselective vinylzincate addition.

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Year:  2007        PMID: 17192109     DOI: 10.1021/ol062737k

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


  12 in total

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Review 2.  Microtubule stabilizing agents as potential treatment for Alzheimer's disease and related neurodegenerative tauopathies.

Authors:  Carlo Ballatore; Kurt R Brunden; Donna M Huryn; John Q Trojanowski; Virginia M-Y Lee; Amos B Smith
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3.  Crotylboron-based synthesis of the polypropionate units of chaxamycins A/D, salinisporamycin, and rifamycin S.

Authors:  Ming Chen; William R Roush
Journal:  J Org Chem       Date:  2012-06-15       Impact factor: 4.354

4.  Streamlined syntheses of (-)-dictyostatin, 16-desmethyl-25,26-dihydrodictyostatin, and 6-epi-16-desmethyl-25,26-dihydrodictyostatin.

Authors:  Wei Zhu; María Jiménez; Won-Hyuk Jung; Daniel P Camarco; Raghavan Balachandran; Andreas Vogt; Billy W Day; Dennis P Curran
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

5.  Phosphate-tether-mediated ring-closing metathesis for the preparation of complex 1,3-anti-diol-containing subunits.

Authors:  Rambabu Chegondi; Soma Maitra; Jana L Markley; Paul R Hanson
Journal:  Chemistry       Date:  2013-05-24       Impact factor: 5.236

6.  A multifaceted phosphate tether: application to the C1-C14 subunit of dolabelides A-D.

Authors:  Joshua D Waetzig; Paul R Hanson
Journal:  Org Lett       Date:  2007-12-07       Impact factor: 6.005

7.  Improved synthesis of 6-epi-dictyostatin and antitumor efficacy in mice bearing MDA-MB231 human breast cancer xenografts.

Authors:  Julie L Eiseman; Lihua Bai; Won-Hyuk Jung; Gustavo Moura-Letts; Billy W Day; Dennis P Curran
Journal:  J Med Chem       Date:  2008-10-08       Impact factor: 7.446

8.  A highly step-economical synthesis of dictyostatin.

Authors:  Stephen Ho; Cyril Bucher; James L Leighton
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-10       Impact factor: 15.336

9.  Synthesis and biological evaluation of (-)-dictyostatin and stereoisomers.

Authors:  Youseung Shin; Jean-Hugues Fournier; Arndt Brückner; Charitha Madiraju; Raghavan Balachandran; Brianne S Raccor; Michael C Edler; Ernest Hamel; Rachel P Sikorski; Andreas Vogt; Billy W Day; Dennis P Curran
Journal:  Tetrahedron       Date:  2007-08-27       Impact factor: 2.457

10.  Efficient syntheses of 25,26-dihydrodictyostatin and 25,26-dihydro-6-epi-dictyostatin, two potent new microtubule-stabilizing agents.

Authors:  María Jiménez; Wei Zhu; Andreas Vogt; Billy W Day; Dennis P Curran
Journal:  Beilstein J Org Chem       Date:  2011-10-05       Impact factor: 2.883

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