Highly efficient solid-phase oxidative cleavage of olefins by OsO 4-NaIO4 in the intramolecular N-acyliminium Pictet-Spengler reaction
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(Chemical Equation Presented) In the present investigation, solid-supported peptide olefins were converted quantitatively to aldehydes via the OsO 4-NaIO4-mediated oxidative cleavage reaction. Addition of DABCO was essential to efficiently suppress the formation of hydroxymethyl ketone side products. The generated aldehydes were used in intramolecular N-acyliminium Pictet-Spengler reactions to produce highly pure pyrroloisoquinoline derivatives. The methodology was extended to allylglycine derivatives to enable the incorporation of pyrroloisoquinoline scaffolds within peptides.
Originalsprog | Engelsk |
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Tidsskrift | Organic Letters |
Vol/bind | 7 |
Udgave nummer | 13 |
Sider (fra-til) | 2695-2698 |
Antal sider | 4 |
ISSN | 1523-7060 |
DOI | |
Status | Udgivet - 2005 |
Eksternt udgivet | Ja |
ID: 326846971