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Synfacts 2010(8): 0969-0969  
DOI: 10.1055/s-0030-1257797
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Silica-Phase Synthesis of Kahalalide B and Its Analogues

Contributor(s): Yasuhiro Uozumi, Aya Tazawa
Y. Li, M. Giulionatti, R. A. Houghten
Torrey Pines Institute for Molecular Studies, Port St. Lucie and San Diego, USA
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

Kahalalide B 4a and its analogues 4b-e were synthesized via solid-phase peptide synthesis on silica and imidazole-catalyzed macrolactonization. Thus, the peptide immobilization onto the functionalized mercaptophenyl silica gel 1 followed by removal of the resin support and the O-protecting group gave the peptide thioester 3. Imidazole (1.5 M) catalyzed the macrolactonization of 3 to afford the corresponding cyclic depsipeptides 4 in 80-98% yield.