472-07-1Relevant academic research and scientific papers
A shorter route to the synthesis of (+)-junenol isojunenol, and their coumarate esters from (-)-santonin
Cardona, Luz,Garcia, Begona,Gimenez, J. Enric,Pedro, Jose R.
, p. 851 - 860 (2007/12/18)
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.
Sulfuric Acid-Catalyzed Cyclization of Germacrene-D to Eudesmane-4,6-diol Cyclic Sulfate
Itokawa, Hideji,Matsumoto, Hajime,Sachio, Nagamine,Totsuka, Nobuo,Watanabe, Kinzo
, p. 3161 - 3163 (2007/10/02)
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.
Synthetic Studies of Terpenoids. Part 7. Synthetic Studies leading to the Total Synthesis of Eudesmane Sesquiterpenoids
Banerjee, Ajoy K.,Hurtado, Hector E.,Carrasco, Maria C. de
, p. 2547 - 2552 (2007/10/02)
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.
