Epoxides trifluoroacetamides

Two derivatives, compound 94, which bears an esperamicin core with an epoxide trigger, and 95, which is a hybrid between esperamicin and dynemicin A cores,have been reported (Scheme 19.25). Both compounds, after trifluoroacetamide removal, underwent cycloaromatization and showed an interesting antitumor activity in vivo in mice. 

A -substituted 2-oxazolidinones (194) are the products of reaction of trifluoroacetamide sodium salts with terminal epoxides or a-hydroxy tosylates (Scheme 97) <92TL377>. When the nitrogen is unsubstituted, the reaction stops before cyclization, presumably because the acetamide N—H is more acidic than the hydroxy group. Tosylation of iV-Boc derivatives of )S-amino alcohols furnishes... 

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