17015-29-1Relevant academic research and scientific papers
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.
