62358-38-7Relevant academic research and scientific papers
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.
