Total synthesis of natural tert-alkylamino hydroxy carboxylic acids

Recent efforts for the total synthesis of natural products with amino hydroxy carboxylic acids is discussed. These products contain quartenary carbon with amino group and they include manzacidins, sphingofungins, lactacystin, kaitocephalin, altemicidin, neoxazolomycin, and tetrodotoxin. The methodologies applied in the construction of quaternary stereogenic centers for these complex molecules include asymmetric Strecker synthesis, nitrene C-H insertion, Lewis-acid-induced Hatakeyama rearrangement, Overman rearrangement, aldol condensation of α-amino ester, iodocyclization of isothiourea, asymmetric allylic alkylation using chira Pd(II) complex, epoxide opening reaction with azide anion, aldol condensation of Schllkop's bislactam and alkylation of oxazoline ester, mercuriocyclization of allylic trichloroacetimidate, Diels-Alder cycloaddition, and Beckmann rearrangement and Michael addition of carbamate to conjugated ester.