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Chemical and Pharmaceutical Bulletin
Vol. 14 (1966) No. 8 P 890-896

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http://doi.org/10.1248/cpb.14.890


Cyperotundone, the constituent of nutgrass (Cyperus rotundus (Cyperaceae)), has been shown to have the stereostructure I as follows : Spectral determinations of it and its derivatives revealed the presence of a 2-methyl-3-substituted cyclopent-2-enone system with a methylene αto the carbonyl. The carbon skeleton was established by transformation to the isopatchoulane (VI) derived from patchouli alcohol (VII). The absolute configuration of the C-11 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 methyl signals.

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