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Salvinorin C (1), a minor component from a biologically active TLC fraction, was isolated from the leaves of the Mexican mint Salvia divinorum. Its structure was elucidated on the basis of extensive proton and C-13 NMR experiments, as well as by comparison of the NMR data with those of the mono- and diacetate derivatives 5-7 of the major NaBH(4)-reduction product of salvinorin A (2). [structure: see text]

Salvinorin C (1), a minor component from a biologically active TLC fraction, was isolated from the leaves of the Mexican mint Salvia divinorum. Its structure was elucidated on the basis of extensive proton and C-13 NMR experiments, as well as by comparison of the NMR data with those of the mono- and diacetate derivatives 5−7 of the major NaBH4-reduction product of salvinorin A (2).

The steric and stereochemical factors which favor the 5-exo cyclization of a 5-substituted 2-sila-5-hexen-1-yl radical have been probed. This radical cyclization approach constitutes a highly efficient and convenient means for the stereospecfic introduction of an angular hydroxymethyl group.