17015-30-4Relevant academic research and scientific papers
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.
REGIO- AND STEREO-SPECIFIC SYNTHESES OF ACHIRAL TERPENOID ALLOMONES AND PHEROMONE COMPONENTS: DENDROLASIN, (E)-β-FARNESENE, AND β-SPRINGENE
Carpita, Adriano,Bonaccorsi, Fabrizio,Rossi, Renzo
, p. 443 - 450 (2007/10/02)
Chemically and stereoisomerically pure dendrolasin (1c), an alarm and defence substance of Lasius fulginosus, has been prepared according to a simple reaction sequence in which the key step involves the reaction of the Grignard reagent derived from 3-(bromomethyl)furan (5) with geranyl acetate (9), in the presence of dilithium tetrachlorocuprate.An analogous reaction has been successfully used to prepare 99percent stereoisomerically pure (Z)-3-(4,8-dimethyl-3,7-nonadienyl)furan (1f) starting from neryl acetate (10).Compound 1c has been also obtained by coupling reaction of 5 with the ?-allylnickel(II) complex derived from geranyl bromide (3).However, in this case 1c was contamined by substantial amounts of 1f.Stereoisomerically pure (E)-β-farnesene (1d), the alarm pheromone of many aphids, has been analogously synthesized by coupling reaction either of the ?-allylnickel halide complex derived from (E)-1-bromo-2-methyl-6-methylene-2,7-octadiene (14) with 1-bromo-3-methyl-2-butene (16), or of ?-(1,1-dimethylallyl)nickel bromide (19) with 14.A similar coupling reaction involving the ?-allylnickel halide derived from 14 and 3 has been employed to prepare β-springene (1e), a diterpene isolated from the dorsal gland of the springbok, Antidorcas marsupialis.
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.
