390386-36-4Relevant academic research and scientific papers
Synthesis of cystothiazole E and formal syntheses of cystothiazoles A and C by Pd0-catalyzed cross-coupling reactions
Bach, Thorsten,Heuser, Stefan
, p. 5585 - 5592 (2007/10/03)
The synthesis of the naturally occurring bithiazole (+)-cystothiazole E (1e) is described starting from oxazolidinone 2. It proceeded in 10 steps and an overall yield of 37%. The key reaction of the sequence was a Suzuki cross-coupling between bromobithia
Total synthesis of cystothiazoles A and C
Williams,Patnaik,Clark
, p. 8463 - 8469 (2007/10/03)
An efficient pathway culminating in the enantiocontrolled preparation of cystothiazoles A and C has been described. The cystothiazoles demonstrate potent antifungal activity and function as novel inhibitors of mitochondrial oxidation at a specific site on the cytochrome bc1 complex. These studies outline a general and flexible plan that can be readily adapted for the synthesis of a variety of related five-membered heterocyclic systems and for biological investigations of structure-activity relationships. The core [2,4′]bisthiazole component 8 was prepared in six steps, and the use of the Horner-Emmons olefination to yield the α,β-unsaturated ester 10 set the stage for an asymmetric Evans aldol process, which established the required C4/C5 stereochemistry. Finally the cystothiazoles A and C were prepared via a stereocontrolled O-alkylation of the precursor β-keto esters 22a and 22b.
