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Paper | Special issue | Vol 54, No. 2, 2001, pp.765-776
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)65
Intramolecular Photocycloaddition of 2-Cycloalkenyl-1,3-dioxin-4-one. Stereoselective Synthesis of cis-Eudesmane-4,11-diols

Toshihide Hatsui,* Ka Li, Akira Mori,* and Hitoshi Takeshita

*Institute of Advanced Material Study, 86 Kyushu University, Kasuga, Fukuoka 816-8580, Japan

Abstract

Two isomeric eudesmane-4,11-diols having a cis-decalin skeleton were synthesized via intramolecular photocycloaddition of 6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,3-dioxin-4-one. Comparison of their NMR spectra with the natural diol, isolated from the Pakistanii medicinal plant, Pluchea arguta (Compositae), indicated that it should be a trans-eudesmanoid.