Lepadiformine: a case study of the value of total synthesis in natural product structure elucidation.
Lepadiformine: a case study of the value of total synthesis in natural product structure elucidation.
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DOI：
10.1021/ar0200403
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发表时间：
2003
影响因子：
18.3
通讯作者：
S. Weinreb
中科院分区：
文献类型：
--
作者：
S. Weinreb
自从二十世纪中叶常规 X 射线晶体学和高场 FT NMR 出现以来，大多数有机化学家都低估了全合成在结构解析中的重要性。然而，光谱方法的局限性和易错性最近因许多复杂天然产物的错误表征而凸显出来，这些天然产物的正确结构最终都是通过全合成确定的。该叙述描述了全合成不仅有助于反驳海洋生物碱 Lepadiformine 的错误结构，而且对于建立正确的结构和绝对构型也至关重要。
Since the emergence of routine X-ray crystallography and high-field FT NMR in the mid-twentieth century, the importance of total synthesis in structure elucidation has become underappreciated by most organic chemists. However, the limitations and fallibility of spectral methodology has recently been highlighted by the mischaracterization of a number of complex natural products, the correct structures of which were all ultimately assigned by total synthesis. This account describes how total synthesis was not only instrumental in disproving the erroneously assigned structure of the marine alkaloid, lepadiformine, but also was also pivotal in establishing the correct structure and absolute configuration.