1. Revision of the Structure and Total Synthesis of Topsentin C.
- Author
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Golantsov, Nikita E., Festa, Alexey A., Varlamov, Alexey V., and Voskressensky, Leonid G.
- Subjects
- *
ALKALOIDS , *CHEMICAL synthesis , *CHEMICAL structure , *CONJUGATE addition reactions , *CHEMICAL precursors , *DIAMINES - Abstract
An efficient synthetic approach to access (indol-3-yl)ethane-1,2-diamines with a protecting group at the indole N atom from readily available 3-(2-nitrovinyl)indoles is reported. This approach includes solvent-free conjugate addition of O-pivaloylhydroxylamines to 1-Boc-3-(2-nitrovinyl)indoles followed by mild reduction of the adducts. The obtained (indol-3-yl)ethane-1,2-diamines are convenient synthetic precursors for several classes of marine alkaloids. The first total synthesis of racemic topsentin C, a secondary metabolite from Hexadella sp., based on this approach is reported. The initially proposed structure for topsentin C has been revised. [ABSTRACT FROM AUTHOR]
- Published
- 2017
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