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Synfacts 2008(2): 0215-0215  
DOI: 10.1055/s-2007-992519
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Click Macrocyclization

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada
R. A. Turner, A. G. Oliver, R. S. Lokey*
University of California at Santa Cruz, USA
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

Cyclic tetra-, penta-, hexa-, and heptapeptides 5a-e were prepared via solid-phase click macrocyclization. Thus, resin-bound peptides 3a-e were prepared from a 2-chlorotrityl resin-supported alkyne 1 via a parallel split-split synthesis. The click macrocyclization of 3b-e with CuBr followed by cleavage from the polymer resin afforded the corresponding macromonomers 5b-e in 20-27% yield (from 3) with small amounts of cyclodimers 6b-e and cyclooligomers.