56694-89-4Relevant academic research and scientific papers
Photooxidation with Simultaneous Reduction of Hydroperoxides with Tetrabutylammonium Borohydride. Synthesis of Perillenal from Myrcene
Baeckstroem, P.,Okecha, S.,Silva, N. de,Wijekoon, D.,Norin, T.
, p. 31 - 36 (2007/10/02)
The synthetic routes to 2-methyl-5-(3-furyl)-2-pentenal, perillenal (1), starting from 2-methyl-6-methylene-2,7-octadiene, myrcene (2), are described.Myrcene (2) was either photooxidized to a mixture of the allylic alcohols 3 and 4 or converted to the aldehyde 11 by oxidation with selenium dioxide followed by chromium trioxide dipyridine in acetic acid.The alcohols 3 and 4 and the aldehyde 11 were cyclized with singlet oxygen to the endoperoxides 5, 6, and 12, respectively.The endoperoxides were converted to the furans 7, 8, and 1 by treatment with Fe(II).The secondary allylic furan 8 was converted to perillenal (1) by a one-step reaction involving an allylic rearrangement and an oxidation with pyridinium chlorochromate in the presence of p-toluenesulfonic acid in dichloromethane.A method for photooxidation and simultaneous reduction of hydroperoxides with tetrabutylammonium borohydride is presented.
