Synthetic enantiopure aziridinomitosenes: preparation, reactivity, and DNA alkylation studies

…, A Klapars, DL Warner, V Li, Y Na, H Kohn

Index: Vedejs, Edwin; Naidu; Klapars, Artis; Warner, Don L.; Li, Ven-Shun; Na, Younghwa; Kohn, Harold Journal of the American Chemical Society, 2003 , vol. 125, # 51 p. 15796 - 15806

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Citation Number: 46

Abstract

An enantiocontrolled route to aziridinomitosenes had been developed from l-serine methyl ester hydrochloride. The tetracyclic target ring system was assembled by an internal azomethine ylide cycloaddition reaction based on silver ion-assisted intramolecular oxazole alkylation and cyanide-induced ylide generation via a labile oxazoline intermediate (62 to 66). Other key steps include reductive detritylation of 26, methylation of the NH aziridine ...