Solid-phase synthesis of biarylalanines via Suzuki cross-coupling and intramolecular N-acyliminium Pictet-Spengler reactions

Tetrahedron Letters

Volumn 46, Issue 46, 2005, Pages 7959-7962

  Nielsen, Thomas E ^a   Le Quement, Sebastian ^a   Meldal, Morten ^a  

^a CARLSBERG LABORATORY   (Denmark)

Author keywords

Biaryl peptides; Scaffold synthesis; Solid phase reaction; Suzuki reaction

Indexed keywords

ALANINE DERIVATIVE; ALDEHYDE; BORONIC ACID DERIVATIVE; IMINE; ISOQUINOLINE DERIVATIVE; PALLADIUM; PEPTIDE DERIVATIVE;

ARTICLE; CATALYSIS; MOLECULAR BIOLOGY; PICTET SPENGLER REACTION; SOLID; SOLID PHASE SYNTHESIS; SUZUKI REACTION;

EID: 26844451459     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.080     Document Type: Article

References (24)

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20. 2 gave clean conversions under a variety of reaction conditions (base/solvent/temperature).
21. If the cross-coupling step was repeated once, the catalyst loading could be lowered to 0.1 equiv in each run, still enabling the quantitative formation of biaryl compounds.
22. 3CN. The resulting solution was filtered through a Teflon filter and analyzed by RP-HPLC and ESMS.
23. The purity of 11e is higher than that of 7e, indicating the presence of insoluble impurities resisting to be washed out of the solid-supported coupling product 8e prior to cleavage from the resin.
24. Selected analytical data for pyrroloisoquinolines