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Selective access to e - And Z -ΔIle-containing peptides via a stereospecific E2 dehydration and an O → N acyl transfer

Organic Letters, ISSN: 1523-7052, Vol: 16, Issue: 15, Page: 4044-4047
2014
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Article Description

A concise synthesis of peptides that contain E- or Z-dehydroisoleucine (ΔIle) residues is reported. The key reaction is an unusual anti dehydration of β-tert-hydroxy amino acid derivatives that is mediated by the Martin sulfurane. A subsequent tandem Staudinger reduction-O → N acyl transfer process forges an amide bond to the ΔIle residue with minimal E/Z alkene isomerization. Density functional calculations attribute the stereospecific dehydration to a highly asynchronous E2 anti process. © 2014 American Chemical Society.

Bibliographic Details

Ma, Zhiwei; Jiang, Jintao; Luo, Shi; Cai, Yu; Cardon, Joseph M; Kay, Benjamin M; Ess, Daniel H; Castle, Steven L

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Chemistry

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