Preakuammicine: A Long-Awaited Missing Link in the Biosynthesis of Monoterpene Indole Alkaloids (Eur. J. Org. Chem. 8/2016)
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- 作者：Sarah Benayad ; Kadiria Ahamada ; Guy Lewin ; Laurent Evanno and Erwan Poupon
- 关键词：Natural products ; Biosynthesis ; Alkaloids ; Biomimetic synthesis ; Sigmatropic rearrangement
- 刊名：European Journal of Organic Chemistry
- 出版年：2016
- 出版时间：March 2016
- 年：2016
- 卷：2016
- 期：8
- 全文大小：9648K
- ISSN：1099-0690
文摘
The cover picture shows a wanted notice for preakuammicine, depicted in the style of a Western movie. The structure was proposed 47 years ago as being a key biosynthetic intermediate in the monoterpene indole alkaloids' biosynthetic pathways. Surprisingly, this missing link has never been described, thus deserving a reward for data. A (16S) stereochemistry was commonly admitted, but does not match the stereochemistry of its postulated biosynthetic precursor. In this paper, the first biomimetic synthesis of the preakuammicine framework is described, affording thereby a complete NMR description. Stereochemical issues are also reconsidered. Details are discussed in the Communication by L. Evanno, E. Poupon et al. on p. lass="accessionId" href="http://dx.doi.org/10.1002/ejoc.201600102" title="Link to external resource: 1494 ff">1494 ff.