Solid Phase Library Synthesis of Cyclic Depsipeptides: Aurilide and Aurilide Analogues
- 18 April 2003
- journal article
- Published by American Chemical Society (ACS) in Journal of Combinatorial Chemistry
- Vol. 5 (4) , 414-428
- https://doi.org/10.1021/cc020091r
Abstract
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.Keywords
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