A Straightforward Route to Novel α,α-Disubstituted Tetrahydrofuran β-Amino Acids and Spirodiketopiperazines from Sugar Lactones

 

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Abstract

Indium-mediated Reformatsky reactions of aldonolactones with ethyl α-bromoisobutyrate allowed the synthesis of ulo­sonic acid esters, which were readily transformed into the corresponding tetrahydrofuran β-azido esters in a stereoselective fashion. This approach provided monomeric components suitable for oligomerization to the carbopeptoid class of foldamers and prompted the total synthesis of the attractive novel spiro diketo­piperazine, which can be regarded as a spironucleoside.

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Azido ester 14; mp 88-90 ˚C (Et₂O-hexane).

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