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Synfacts 2006(2): 0181-0181  
DOI: 10.1055/s-2005-921768
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid-Phase Synthesis of Pyrroloisoquinoline

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Takayasu Arakawa
T. E. Nielsen, S. L. Quement, M. Meldal*
SPOCC Centre, Valby, Denmark
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

Solid-phase decoration of the pyrroloisoquinoline scaffold via the Suzuki reaction was demonstrated. Solid-supported masked peptide aldehydes 1, containing 3- or 4-iodophenyl­alanine residues, were coupled with several arylboronic acids to give biarylalanines 2. The resulting biarylalanines 2 were converted into the desired pyrroloisoquinolines 3 of >85% purity via TFA-mediated intramolecular N-acyliminium Pic­tet-Spengler reactions and cleavage of the resin supports (28 examples).