Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates
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(Chemical Equation Presented) A general strategy for the solid-phase synthesis of structurally diverse bicyclic dipeptide mimetics is presented. Depending on the amino acid side-chain (R1), peptide-derived N-acyliminium intermediates may undergo nucleophilic attack from either side-chain functional groups (-OH, -NH2, -SH, and -CONH2) or the amide backbone (-CONH-) of the peptide, thus affording a range of aza-, thia-, and oxabicycloalkanes in excellent purity and diastereoselectivity.
Originalsprog | Engelsk |
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Tidsskrift | Organic Letters |
Vol/bind | 7 |
Udgave nummer | 17 |
Sider (fra-til) | 3601-3604 |
Antal sider | 4 |
ISSN | 1523-7060 |
DOI | |
Status | Udgivet - 18 aug. 2005 |
Eksternt udgivet | Ja |
ID: 326847053