17015-30-4Relevant articles and documents
Narcissus trevithian and Narcissus geranium: Analysis and Synthesis of Compounds
Dort, Hans M. van,Jaegers, Paul P.,Heide, Roel ter,Weerdt, Anton J. A. van der
, p. 2063 - 2075 (2007/10/02)
The essential oils of two narcissus varieties, Narcissus trevithian and Narcissus geranium, obtained by extraction of flowers followed by high vacuum distilation of the absolute, were analyzed by GC/MS.After separation in fractions, unknown compounds were isolated by preparative GLC and their structures established by NMR/IR spectroscopy.The synthesis of a number of new compounds, found for the first time in narcissus oil, is described.The two narcissus species are compared with respect to their main components and odor quality.All compounds found so far in narcissus varieties are listed.
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.