David, Nadege; Pasceri, Raffaele; Kitson, Russell R. A.; Pradal, Alexandre; Moody, Christopher J. published an article in 2016, the title of the article was Formal total synthesis of diazonamide A by indole oxidative rearrangement.COA of Formula: C6H10Cl3NO And the article contains the following content:
A short formal total synthesis of the marine natural product diazonamide A is described. The route is based on indole oxidative rearrangement, and a number of options were investigated involving migration of tyrosine or oxazole fragments upon oxidation of open chain or macrocyclic precursors. The final route proceeds from 7-bromoindole by sequential palladium-catalyzed couplings of an oxazole fragment at C-2, followed by a tyrosine fragment at C-3. With the key 2,3-disubstituted indole readily in hand, formation of a macrocyclic lactam set the stage for the crucial oxidative rearrangement to a 3,3-disubstituted oxindole. Notwithstanding the concomitant formation of the unwanted indoxyl isomer, the synthesis successfully delivered, after deprotection, the key oxindole intermediate, thereby completing a formal total synthesis of diazonamide A. The experimental process involved the reaction of tert-Butyl trichloroacetimidate(cas: 98946-18-0).COA of Formula: C6H10Cl3NO
The Article related to natural product diazonamide a synthon total synthesis macrocyclic peptidomimetic, peptide coupling iodination oxazole tyrosine indole oxidative rearrangement macrocyclization, natural products, oxindoles, total synthesis and other aspects.COA of Formula: C6H10Cl3NO
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics