Literature DB >> 26120213

Enantioselective synthesis of metacycloprodigiosin via the "Wasserman pyrrole".

Marvin M Vega1, Diana M Crain1, Leah C Konkol1, Regan J Thomson1.   

Abstract

A concise, nine-step enantioselective total synthesis of metacycloprodigiosin is reported. The synthesis provides increased step-efficiency over the previous racemic and enantioselective syntheses of this compound. Key features of the work include investigations into a convergent oxidative coupling reaction and subsequent ring-closing metathesis to deliver an advanced pyrrole intermediate we name the "Wasserman pyrrole" that can be converted to metacycloprodigiosin in one step.

Entities:  

Keywords:  Metacycloprodigiosin; Oxidative coupling; Prodigiosin alkaloids; Ring-closing metathesis

Year:  2015        PMID： 26120213      PMCID： PMC4480779          DOI： 10.1016/j.tetlet.2014.12.075

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  21 in total

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3.  Enantioselective organocatalytic singly occupied molecular orbital activation: the enantioselective alpha-enolation of aldehydes.

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4.  The synthesis of metacycloprodigiosin.

Authors:  H H Wasserman; D D Keith; J Nadelson
Journal:  J Am Chem Soc       Date:  1969-02-26       Impact factor: 15.419

5.  Evaluation of the biosynthetic proposal for the synthesis of marineosins A and B.

Authors:  Leslie N Aldrich; Eric S Dawson; Craig W Lindsley
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6.  A concise synthesis of butylcycloheptylprodigiosin.

Authors:  Jonathan T Reeves
Journal:  Org Lett       Date:  2007-04-18       Impact factor: 6.005

Review 7.  The biosynthesis and regulation of bacterial prodiginines.

Authors:  Neil R Williamson; Peter C Fineran; Finian J Leeper; George P C Salmond
Journal:  Nat Rev Microbiol       Date:  2006-12       Impact factor: 60.633

8.  Catalytic asymmetric synthesis of acyclic arrays by tandem 1,4-addition-aldol reactions.

Authors:  Gareth P Howell; Stephen P Fletcher; Koen Geurts; Bjorn ter Horst; Ben L Feringa
Journal:  J Am Chem Soc       Date:  2006-11-22       Impact factor: 15.419

9.  Flexible Synthesis of Metacycloprodigiosin and Functional Derivatives Thereof.

Authors:  Alois Fürstner; Helga Krause
Journal:  J Org Chem       Date:  1999-10-29       Impact factor: 4.354

10.  Anticancer and immunosuppressive properties of bacterial prodiginines.

Authors:  Neil R Williamson; Peter C Fineran; Tamzin Gristwood; Suresh R Chawrai; Finian J Leeper; George P C Salmond
Journal:  Future Microbiol       Date:  2007-12       Impact factor: 3.165
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  2 in total

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Review 2.  Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products.

Authors:  Dennis X Hu; David M Withall; Gregory L Challis; Regan J Thomson
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  2 in total

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