Department of Chemistry, Boston University, Boston, Massachusetts 02215, USA.
Org Lett. 2010 Aug 6;12(15):3453-5. doi: 10.1021/ol101252y.
A convergent, efficient synthesis of syringolin A has been accomplished in 13 steps from commercially available materials, Garner's aldehyde and L-valine. The unnatural 3,4-dehydrolysine fragment was prepared using successive Johnson-Claisen/Curtius rearrangement reactions. The macrolactamization and late-stage introduction of the side chain will provide convenient access to analogues of this promising proteasome inhibitor.
已经从商业可得的材料（Garner 醛和 L-缬氨酸）出发，通过 13 步反应完成了对 syringolin A 的收敛、高效合成。使用连续的 Johnson-Claisen/Curtius 重排反应制备了非天然的 3,4-脱氢赖氨酸片段。大环内酯化和后期侧链的引入将为这种有前途的蛋白酶体抑制剂的类似物提供便利的途径。
