Department of Chemistry, University of Zurich , 8057 Zurich, Switzerland.
Org Lett. 2017 Jul 21;19(14):3915-3918. doi: 10.1021/acs.orglett.7b01822. Epub 2017 Jul 11.
The synthesis of the presumed structure of aeruginosin KT608A was accomplished for the first time. The unusual d-diepi-Choi core was prepared from tyrosine via C-H activation and heterogeneous hydrogenation. Due to differences in the spectral data of synthetic and natural samples, a revised structure featuring l-diepi-Choi was proposed, which was synthesized and confirmed to be identical. On the basis of these findings, revised structures for six additional aeruginosins (KT608B, KT650, GH553, DA495A, DA511, and KB676) are presented.
首次完成了推定结构的 Aeruginosin KT608A 的合成。通过 C-H 活化和非均相氢化，从酪氨酸制备了不寻常的 d-diepi-Choi 核心。由于合成和天然样品的光谱数据存在差异，提出了一个具有 l-diepi-Choi 的修订结构，该结构已被合成并证实是相同的。基于这些发现，提出了另外六种 Aeruginosins（KT608B、KT650、GH553、DA495A、DA511 和 KB676）的修订结构。
