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Revision of the Structure and Total Synthesis of Topsentin C.

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 -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 sp., based on this approach is reported. The initially proposed structure for topsentin C has been revised.

SUBMITTER: Golantsov NE

PROVIDER: S-EPMC6193241 | biostudies-other | 2017 Jun

REPOSITORIES: biostudies-other

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