Solid Phase Library Synthesis of Cyclic Depsipeptides: Aurilide and Aurilide Analogues

Autor: Takayuki Doi, Andrew M. Bray, Takashi Takahashi, Hiroyuki Nagamiya, Peter G. Griffiths
Jazyk: angličtina
Rok vydání: 2003
Předmět:
Zdroj: Journal of Combinatorial Chemistry. 5(4):414-428
ISSN: 1520-4766
Popis: 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.
Databáze: OpenAIRE
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