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Org Lett. 2014 Feb 7;16(3):792-5. doi: 10.1021/ol4035269. Epub 2014 Jan 10.
An efficient, two-step construction of highly complex alkaloid-like compounds from the natural product fumagillol is described. This approach, which mimics a biosynthetic cyclase/oxidase sequence, allows for rapid and efficient structure elaboration of the basic fumagillol scaffold with a variety of readily available coupling partners. Mechanistic experiments leading to the discovery of an oxygen-directed oxidative Mannich reaction are also described.
本文描述了一种从天然产物呋咱并[1,2-α]色满醇出发高效、两步构建高度复杂类似生物碱化合物的方法。这种方法模拟了生物合成环化酶/氧化酶序列,可快速有效地对呋咱并[1,2-α]色满醇基本骨架进行结构修饰,且可使用各种易得的偶联试剂。文中还描述了导致发现定向氧的氧化 Mannich 反应的机理实验。