22459-10-5Relevant academic research and scientific papers
A Synthesis of trans-β-Farnesene from Myrcene which Includes a Modified Work up Method for Dibah Reductions of Esters to Aldehydes
Baeckstroem, Peter,Li, Lanna,Wickramaratne, Mahinda,Norin,Torbjoern
, p. 423 - 429 (2007/10/02)
A simple synthesis of trans-β-farnesene, an alarm pheromone for aphids, from myrcene is described and a reliable procedure for working up of DIBAH reduction from esters to aldehydes is introduced.
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.
