Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2010(8): 0969-0969
DOI: 10.1055/s-0030-1257797
DOI: 10.1055/s-0030-1257797
Polymer-Supported Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Silica-Phase Synthesis of Kahalalide B and Its Analogues
Y. Li, M. Giulionatti, R. A. Houghten
Torrey Pines Institute for Molecular Studies, Port St. Lucie and San Diego, USA
Further Information
Publication History
Publication Date:
22 July 2010 (online)
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.