Literature DB >> 17439221

A concise synthesis of butylcycloheptylprodigiosin.

Jonathan T Reeves1.   

Abstract

A short and efficient total synthesis of the tripyrrole alkaloid butylcycloheptylprodigiosin is described. Key to the brevity of the approach is a two-step synthesis of macrocyclic formylpyrrole 4 from cyclononenone 6.

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Year:  2007        PMID： 17439221     DOI： 10.1021/ol070341i

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


  7 in total

1.  Elimination of butylcycloheptylprodigiosin as a known natural product inspired by an evolutionary hypothesis for cyclic prodigiosin biosynthesis.

Authors:  Brian T Jones; Dennis X Hu; Brett M Savoie; Regan J Thomson
Journal:  J Nat Prod       Date:  2013-09-20       Impact factor: 4.050

2.  Enantioselective synthesis of metacycloprodigiosin via the "Wasserman pyrrole".

Authors:  Marvin M Vega; Diana M Crain; Leah C Konkol; Regan J Thomson
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

3.  Enantioselective total synthesis and confirmation of the absolute and relative stereochemistry of streptorubin B.

Authors:  Dennis X Hu; Michael D Clift; Kiel E Lazarski; Regan J Thomson
Journal:  J Am Chem Soc       Date:  2010-12-17       Impact factor: 15.419

4.  Development of a merged conjugate addition/oxidative coupling sequence. Application to the enantioselective total synthesis of metacycloprodigiosin and prodigiosin R1.

Authors:  Michael D Clift; Regan J Thomson
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

5.  Ion Mobility Mass Spectrometry as an Efficient Tool for Identification of Streptorubin B in Streptomyces coelicolor M145.

Authors:  Andrew P Marshall; Andrew R Johnson; Marvin M Vega; Regan J Thomson; Erin E Carlson
Journal:  J Nat Prod       Date:  2020-01-06       Impact factor: 4.050

Review 6.  Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products.

Authors:  Dennis X Hu; David M Withall; Gregory L Challis; Regan J Thomson
Journal:  Chem Rev       Date:  2016-06-17       Impact factor: 60.622

Review 7.  Electrophilic Aminating Agents in Total Synthesis.

Authors:  Lauren G O'Neil; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-06       Impact factor: 16.823
  7 in total

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