Literature DB >> 12196986

Biosynthesis inspired Diels-Alder route to pyridines: synthesis of the 2,3-dithiazolylpyridine core of the thiopeptide antibiotics.

Christopher J Moody1, Rachael A Hughes, Stewart P Thompson, Lilian Alcaraz.   

Abstract

Reaction of serine derived 1-alkoxy-2-azadienes with dehydroalanine derived dienophiles results in Diels-Alder reaction and aromatisation to give 2,3,6-trisubstituted pyridines, thereby establishing the viability of the proposed biosynthetic route to the pyridine ring of the thiopeptide antibiotics originally proposed by Bycroft and Gowland.

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Year:  2002        PMID： 12196986     DOI： 10.1039/b204868j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  8 in total

Review 1.  Dehydroamino acids: chemical multi-tools for late-stage diversification.

Authors:  Jonathan W Bogart; Albert A Bowers
Journal:  Org Biomol Chem       Date:  2019-04-10       Impact factor: 3.876

2.  Thiopeptide Pyridine Synthase TbtD Catalyzes an Intermolecular Formal Aza-Diels-Alder Reaction.

Authors:  Jonathan W Bogart; Albert A Bowers
Journal:  J Am Chem Soc       Date:  2019-01-22       Impact factor: 15.419

3.  Interception of the Bycroft-Gowland Intermediate in the Enzymatic Macrocyclization of Thiopeptides.

Authors:  Jonathan W Bogart; Nicholas J Kramer; Aneta Turlik; Rachel M Bleich; Daniel S Catlin; Frank C Schroeder; Satish K Nair; R Thomas Williamson; K N Houk; Albert A Bowers
Journal:  J Am Chem Soc       Date:  2020-07-16       Impact factor: 15.419

4.  Natural products version 2.0: connecting genes to molecules.

Authors:  Christopher T Walsh; Michael A Fischbach
Journal:  J Am Chem Soc       Date:  2010-03-03       Impact factor: 15.419

5.  Chemoenzymatic synthesis of thiazolyl peptide natural products featuring an enzyme-catalyzed formal [4 + 2] cycloaddition.

Authors:  Walter J Wever; Jonathan W Bogart; Joshua A Baccile; Andrew N Chan; Frank C Schroeder; Albert A Bowers
Journal:  J Am Chem Soc       Date:  2015-03-10       Impact factor: 15.419

6.  Total synthesis and complete structural assignment of thiocillin I.

Authors:  Virender S Aulakh; Marco A Ciufolini
Journal:  J Am Chem Soc       Date:  2011-03-29       Impact factor: 15.419

Review 7.  Thiopeptide antibiotics: retrospective and recent advances.

Authors:  Xavier Just-Baringo; Fernando Albericio; Mercedes Álvarez
Journal:  Mar Drugs       Date:  2014-01-17       Impact factor: 5.118

8.  Synthesis of the heterocyclic core of the D-series GE2270.

Authors:  Christophe Berini; Thibaut Martin; Pierrik Lassalas; Francis Marsais; Christine Baudequin; Christophe Hoarau
Journal:  Beilstein J Org Chem       Date:  2017-07-17       Impact factor: 2.883
  8 in total

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