Sarah Benayad, Kadiria Ahamada, Guy Lewin, Laurent Evanno* and Erwan Poupon*

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.

http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201690014/abstract