An Improved Synthesis of Pyridine-thiazole Cores of Thiopeptide Antibiotics

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2009 Jul 4

PMID 19572592

Citations 5

Authors

Virender S Aulakh

Marco A Ciufolini

Affiliations

Soon will be listed here.

Abstract

The oxidation of 2-methylthiazoles to 2-formylthiazoles simplifies the implementation of the Bagley variant of the Bohlmann-Rahtz reaction as a key step in a concise new route to pyridine cores of thiopeptide antibiotics.

Citing Articles

Therapies from Thiopeptides.

Hwang H, Ciufolini M Molecules. 2023; 28(22).

PMID: 38005301 PMC: 10673184. DOI: 10.3390/molecules28227579.

Transition metal(II) complexes of a novel symmetrical benzothiazole-based ligand: synthesis, spectral/structural characterization and fluorescence properties.

Gulcan M, Karatas Y, Isik S, Ozturk G, Akbas E, Sahin E J Fluoresc. 2014; 24(6):1679-86.

PMID: 25212791 DOI: 10.1007/s10895-014-1455-3.

One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor.

Bagley M, Fusillo V, Jenkins R, Lubinu M, Mason C Beilstein J Org Chem. 2013; 9:1957-68.

PMID: 24204407 PMC: 3817555. DOI: 10.3762/bjoc.9.232.

Total synthesis and complete structural assignment of thiocillin I.

Aulakh V, Ciufolini M J Am Chem Soc. 2011; 133(15):5900-4.

PMID: 21446660 PMC: 3077036. DOI: 10.1021/ja110166x.

Bohlmann-Rahtz cyclodehydration of aminodienones to pyridines using N-iodosuccinimide.

Bagley M, Glover C Molecules. 2010; 15(5):3211-27.

PMID: 20657473 PMC: 6263277. DOI: 10.3390/molecules15053211.