Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates

Thomas E. Nielsen, Sebastian Le Quement, Morten Meldal*

*Corresponding author af dette arbejde

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

51 Citationer (Scopus)

Abstract

(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.

OriginalsprogEngelsk
TidsskriftOrganic Letters
Vol/bind7
Udgave nummer17
Sider (fra-til)3601-3604
Antal sider4
ISSN1523-7060
DOI
StatusUdgivet - 18 aug. 2005
Udgivet eksterntJa

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