Moody, Christopher J.; Bagley, Mark C. published the artcile< Total synthesis of (+)-nostocyclamide>, Application of C12H18N2O4S, the main research area is nostocyclamide macrocyclic peptide total synthesis.
The synthesis of (+)-nostocyclamide (I) from the oxazole II and thiazoles III (R = H, CHMe2; Boc = Me3CO2C) is described. The oxazole amino ester II was prepared from N-protected alaninamide using a rhodium(II) catalyzed N-H insertion reaction as a key step, and the thiazoles III were obtained using a modified Hantzsch reaction. The synthesis was completed in six further steps in which fragments II and III (R = CHMe2) were coupled using mixed anhydride methodol. to give a oxazole-thiazole intermediate, deprotection of which and coupling to III (R = H) gave a linear bis-thiazole oxazole intermediate. Macrocyclization using the pentafluorophenyl ester method gave (+)-nostocyclamide I. The synthesis confirms that the natural product is the (+)-enantiomer and has the (2S,12R) absolute configuration.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry published new progress about 96929-05-4. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Application of C12H18N2O4S.
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica