Literature DB >> 20104892

An efficient synthesis of (+/-)-trichostatic Acid and analogues: a new route to (+/-)-trichostatin A.

Anamitra Chatterjee1, Joshua Richer, Tyler Hulett, Vijaya Bhaskara Reddy Iska, Olaf Wiest, Paul Helquist.   

Abstract

An efficient synthesis of rac-trichostatic acid (1) and its analogues is reported starting from a commercially available aldehyde. Further manipulations of rac-1 led to rac-trichostatin A (TSA). Construction of the desired molecular architecture entails a two-component union, achieved through an in situ hydroboration followed by a Suzuki-Miyaura coupling with 2. The requisite homopropargyl alcohol was synthesized by exploiting allenylindium chemistry. This new protocol paved the way for the synthesis of analogues of trichostatic acid and hence TSA.

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Year:  2010        PMID: 20104892     DOI: 10.1021/ol9029116

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


  2 in total

1.  Asymmetric propargylation of ketones using allenylboronates catalyzed by chiral biphenols.

Authors:  David S Barnett; Scott E Schaus
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

2.  Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2012-06-25       Impact factor: 15.419

  2 in total

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