Structure and Absolute Configuration of Cyperotundone

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Abstract
Cyperotundone, the constituent of nutgrass (Cyperus rotundus (Cyperaceae)), has the stereostructure I as follows: Spectral determinations of it and its derivatives revealed the presence of a 2-methyl-3-substituted cyclo-pent-2-enone system with a methylene a to the carbonyl. The carbon skeleton was established by transformation to the isopatchoulane (VI) derived from patchouli alcohol (VTI). The absolute configuration of the C-ll bridge was deduced from the above transformation and a positive Cotton effect of the optical rotatory dispersion of the ketone (X) and that of the C-10 methyl from examination of the NMR [nuclear magnetic resonance spectral] methyl signals.

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