Solid phase library synthesis of cyclic depsipeptides: Aurilide and aurilide analogues

Takashi Takahashi, Hiroyuki Nagamiya, Takayuki Doi, Peter G. Griffiths, Andrew M. Bray

Research output: Contribution to journalArticlepeer-review

51 Citations (Scopus)


A solid-phase combinatorial synthesis approach toward the cyclic depsipeptide aurilide (1) and related analogues is described. The peptide moiety 2 was assembled on trityl linker-functionalized SynPhase Crowns using an Fmoc strategy. Optimization of the tetrapeptide assembly 5 was carried out using parallel multiple synthesis and LC/MS analysis. The aliphatic moiety 3a was coupled with the solid-supported 2 using DIC/HOBt. Following deprotection and cleavage of linear precursor 26, macrocyclization was achieved under high dilution conditions. Removal of the methylthiomethyl protecting group provided aurilide (1) in 11% overall yield. Synthesis of a combinatorial library of aurilide derivatives 4 was accomplished with a similar protocol using the TranSort technique.

Original languageEnglish
Pages (from-to)414-428
Number of pages15
JournalJournal of Combinatorial Chemistry
Issue number4
Publication statusPublished - 2003 Jul


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