Epoc group: transformable protecting group with gold(iii)-catalyzed fluorene formation
Tomoya Yamamoto1, Tsung-Che Chang1, Katsunori Tanaka1,2,3
1Biofunctional Synthetic Chemistry Laboratory, RIKEN Cluster for Pioneering Research 2-1 Hirosawa, Wako-shi Saitama 351-0198 Japan kotzenori@riken.jp.
Abstract:
This study presents the novel concept of a transformable protecting group, which changes its properties through structural transformation. Based on this concept, we developed a 2-(2-ethynylphenyl)-2-(5-methylfuran-2-yl)-ethoxycarbonyl (Epoc) group. The Epoc group was transformed into an Fmoc-like structure with gold(iii)-catalyzed fluorene formation and was removable under Fmoc-like mild basic conditions post-transformation even though it was originally stable under strongly basic conditions. As an application for organic synthesis, the Epoc group provides the novel orthogonality of gold(iii)-labile protecting groups in solid-phase peptide synthesis. In addition, the high turnover number of fluorene formation in aqueous media is suggestive of the applicability of the Epoc group to biological systems.
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