138667-71-7Relevant academic research and scientific papers
Total synthesis of thiangazole
Akaji, Kenichi,Kiso, Yoshiaki
, p. 10685 - 10694 (2007/10/03)
A method for total synthesis of thiangazole (1), a tris-thiazoline- oxazole metabolite, is described. The key intermediate 9, a linear tetrapeptide amide composed of three S-benzyl-2-methylcysteine residues and a O-benzyl-threonine amide, was synthesized in 4 steps using 2-chloro-1,3- dimethyl-imidazolidium hexafluorophosphate(CIP)mediated activation. The successive thiazoline/oxazole rings were constructed by TiCl4mediated cycledehydration followed by acid-catalyzed Robinson-Gabriel reaction without difficulty.
Chemical modification of thiangazole A in the oxazole and styryl region
Herrmann, Martina,Ehrler, Juerg,Kayser, Hartmut,Rindlisbacher, Alfred,Hoefle, Gerhard
, p. 3381 - 3392 (2007/10/03)
The partial synthesis of 54 derivatives of thiangazole A (1a), a new polythiazoline antibiotic from Polyangium spec. (myxobacteria), is described. Derivatives with chemical modification of the carboxamide group in the oxazole region were prepared either by N-alkylation to amides 5-14 or by methanolysis to ester 15, and its transformation products 16, 19, 20. Oxidation of the C-5 methyl group of 1a with molecular oxygen led to the hydroxymethyl derivative 21, and two by-products lacking the C-5 methyl group (22), or the entire oxazole ring (23). Key intermediate for analogues with modifications in the styryl region is the aldehyde 27, obtained by direct cleavage of the C-21/C-22 double bond. 27 was transformed into the oximes 37- 42 and by Wittig reaction to (21Z)-thiangazole (43) and analogues 44-46 with proton and alkyl residues replacing phenyl. 21,22-Didehydrothiangazo1e (50) was synthesized in a multi-step reaction from 27 via the 20-alkinyl intermediate 49. The insecticidal activities and inhibition of the respiratory chain (complex I) by the thiangazole analogues were determined and compared with the natural product.
From Aziridines to Oxazolines and Thiazolines: The Heterocyclic Route to Thiangazole
Wipf, Peter,Venkatraman, Srikanth
, p. 1 - 10 (2007/10/03)
Since its isolation in 1991, the polyazole natural product thiangazole has become a popular target for total synthesis due to its challenging array of heterocyclic segments and its reported potent antiviral activity. The synthetic activity toward thiangazole is reviewed and a novel approach that takes advantage of aziridine and oxazoline intermediates en route to thiazolines is presented.
Natural Products as Pesticides: Two Examples of Stereoselective Synthesis
Frueh, Thomas,Chemla, Philippe,Ehrler, Juerg,Farooq, Saleem
, p. 37 - 48 (2007/10/03)
The strategy and synthetic efforts leading to efficient stereoselective syntheses of thiangazole, a tris-thiazolinyl-oxazole metabolite isolated from Polyangium spp., and hydantocidin, a spironucleoside metabolite isolated from Streptomyces hygroscopicus, are discussed.
Total synthesis of thiangazole, a novel naturally occurring HIV-1 inhibitor from Polyangium sp
Boyce, Richard J.,Mulqueen, Gerard C.,Pattenden, Gerald
, p. 7321 - 7330 (2007/10/02)
The total synthesis of the cinnamyl-oxazole substituted tris-thiazoline containing metabolite (-)-thiangazole (1) is described. The synthesis is based on elaboration of the R-2-methylcysteine derived bis-thiazoline nitrile (5) and oxazole (6) intermediate
Total Synthesis of (-)-Thiangazole and Structurally Related Polyazoles
Wipf, Peter,Venkatraman, Srikanth
, p. 7224 - 7229 (2007/10/03)
Thiangazole was reported to be an extremely potent, nontoxic inhibitor of HIV-1 in MT4 cell assays.By employing a strategy of selective oxazoline-thiazoline interconversions, we have accomplished a total synthesis of the natural product in 16 steps and 1.1percent overall yield from (S)-α-methylserine.This new methodology is especially useful for the preparation of analogs of thiangazole and structure-activity studies.Our preliminary biological testing of (-)-thiangazole revealed a high level of cytotoxicity that was considerably reduced in the oxazoline-containing analogs.
Total synthesis of thiangazole, a novel inhibitor of HIV-1 from Polyangium sp
Boyce, Richard J.,Mulqueen, Gerard C.,Pattenden, Gerald
, p. 5705 - 5708 (2007/10/02)
A concise total synthesis of the cinnamyl-oxazole substituted tris- thiazoline containing metabolite thiangazole 1 is described.
