- A shorter route to the synthesis of (+)-junenol isojunenol, and their coumarate esters from (-)-santonin
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This paper reports on the chemical conversion of (-)-santonin into (+)-junenol, isojunenol and their coumarate esters. The identity of (+)-junenol and 8-epi-β-verbesinol is also established.
- Cardona, Luz,Garcia, Begona,Gimenez, J. Enric,Pedro, Jose R.
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p. 851 - 860
(2007/12/18)
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- Sulfuric Acid-Catalyzed Cyclization of Germacrene-D to Eudesmane-4,6-diol Cyclic Sulfate
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Reaction of germacrene-D with sulfuric acid afforded a eudesmane-4,6-diol cyclic sulfate (1).The structure of 1 was determined by spectral analysis and chemical correlations.
- Itokawa, Hideji,Matsumoto, Hajime,Sachio, Nagamine,Totsuka, Nobuo,Watanabe, Kinzo
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p. 3161 - 3163
(2007/10/02)
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- Synthetic Studies of Terpenoids. Part 7. Synthetic Studies leading to the Total Synthesis of Eudesmane Sesquiterpenoids
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The synthesis of two naturally occuring sesquiterpenes, (+/-)-junenol (1) and (+/-)-acolamone (2), from the bicyclic ketone (3) is described.The introduction of an isopropyl chain at C-7 of the bicyclic ketone was attempted by three different procedures and yielded ketone (5) which, on reduction with sodium and ethanol, gave the alcohol (12).This, on oxidation with lead tetra-acetate and iodine in cyclohexane, yielded the cyclic ether (13) and regenerated the ketone (5).Oxidation of compound (13) with chromium(VI) oxide in acetic acid afforded the keto-acid (15) which, on oxidative decarboxylation with lead tetra-acetate, furnished acolamone which was reduced with sodium borohydride in ethanol to (+/-)-junenol.
- Banerjee, Ajoy K.,Hurtado, Hector E.,Carrasco, Maria C. de
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p. 2547 - 2552
(2007/10/02)
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