Artemisia fragrans

Though the triplet sensitized photolysis of isoprene (159) does, as noted above, produce a complex mixture of products, one of these adducts has been used in the context of complex molecule synthesis (equation 5)71. Cyclobutane 160, which was formed in ca 20% yield by the benzophenone sensitized photolysis of 159, could be easily transformed into fragrantolol, 161, an isomer of grandisol isolated from the roots of the Artemisia fragrans, by simple hydroboration/oxidation of the less hindered double bond. 

C,oH,80,Mr 154.25, oil, bp. 120°C(1.2 kPa). Mono-terpene with cyclobutane structure, C-1 epimer of grandisol, known as the sexual pheromone of the male boll weevil. It is not known if F. possesses the same biological activity. F. occurs in the roots of the mug-wort species Artemisia fragrans (Asteraceae), content 0.0033%. ... 

Bohlmann, F., C. Zdero und U. Faass Uber die Inhaltsstoffe von Artemisia fragrans Willd. Ber. dtsch. chem. Ges. 106, 2904 (1973). 

Fragranol (85), a cyclobutane derivative, has been obtained from root of Artemisia fragrans, where several of its esters are also present (54). Eucarvone (86), which was isolated in 1905 (379) occurs in the essential oil from rhizomes of Asarum sieboldii. Two related compounds are the carboxylic acids, shonanic acid (87) from the wood of Libocedrus formosana and thujic acid (88) present in the heartwood of Thuja plicata, which also contains its methyl ester (140). 

Bohlmann F, Zdero C, Faass U 1973 Ober die Inhaltsstoffe von Artemisia fragrans Willd. Chem Ber 106 2904-2909... 

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