Representative elemanoids, geijerone (4) and γ-elemene (5), were synthesised in racemic form via reductive fragmentation of 4β-methylsutphonyloxy-4,4a,5,6,8,8aα-hexahydro-1α,4aβ-dimethylnaphthalene-2,7(1H,3H)-dione 7-ethylene acetal (10) or 2β-hydroxy-4β-methylsulphonyloxy-2,3,4,4a,5,6,8,8aα-octahydro-1α,4aβ-dimethylnaphthalen-7(1H)-one ethylene acetal,(11), both readily available from the Wieland–Miescher ketone (3).
M. Kato, H. Kurihara and A. Yoshikoshi, J. Chem. Soc., Perkin Trans. 1, 1979, 2740 DOI: 10.1039/P19790002740
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