Insect pheromones and their analogs

Odinokov, V. N.; Куковинец, О. С.; Zainullin, R. A.; Tsyglintseva, E. Yu.; Sultanmuratova, V. R.; Веселовский, В. В.; Dragan, V. A.; Rubinskaya, T. Ya.; Cheskis, B. A.; Moiseenkov, A. M.; Толстиков, Г. А.

doi:10.1007/bf00597722

Cited by 2 publications

(3 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Minor variations involving different methods of removing the allylic leaving group were later published. 22 3.1.3 Esters of lavandulol and related compounds. The vine mealybug pheromone (S)-36, the minor component of the pink hibiscus mealybug pheromone (2R,2 0 S)-37, and both components of the banana mealybug pheromone ((R)-38 and (R)-39) are all esters of lavandulol.…”

Section: Overview Of Scale and Mealybug Pheromonesmentioning

confidence: 99%

Chemistry of the pheromones of mealybug and scale insects

Zou

Millar

2015

Nat. Prod. Rep.

View full text Add to dashboard Cite

show abstract

Section: Overview Of Scale and Mealybug Pheromonesmentioning

confidence: 99%

Chemistry of the pheromones of mealybug and scale insects

Zou

Millar

2015

Nat. Prod. Rep.

View full text Add to dashboard Cite

show abstract

“…Claisen rearrangement of the resulting triene alcohol 229 gave ester 15, low-temperature hydride reduction of which with subsequent Wittig olefination of aldehyde 230 by isopropylidenetriphenylphosphorane led to the desired sesquiterpene 231. The synthetic pathway for α-geranylpropionate (235), a component of the sex pheromone of the San Jose scale (Quadraspidiotus perniciosus), that is based on isomerization of the isopropylidene groups of geraniol into an isopropenyl group is interesting [72,73]. Two approaches were used for this.…”

Section: Ozonolysismentioning

confidence: 99%

“…An original approach to the synthesis of ipsdienol (73), an aggregation pheromone of Ips bark beetles, was based on myrcene (71) [29]. Regioselective epoxidation of triene (71) at the ∆ 6,7 -bond formed the epoxide 72, in which the oxirane ring was opened by MeMgI at room temperature after 1 d to give the target pheromone 73.…”

Section: Monoterpenoids Functionalized By Epoxidationmentioning

confidence: 99%

Insect Pheromones Synthesized by Oxidative Transformations of Natural Monoterpenoids

et al. 2005

Self Cite

View full text Add to dashboard Cite

The literature on oxidative transformations of natural monoterpenoids to synthesize insect pheromones was reviewed.The literature on pheromone chemistry is broad and reflects the consistent interest in this area over the last 20 years in the form of monographs [1-7] and reviews [8][9][10][11][12][13][14][15].Insect pheromones known today are rather simple molecules (less than four asymmetric centers and four functional groups). Therefore, the "ideal" substrate (chiral or achiral) for most such structures is a moderately functionalized molecule, in particular, hydroxy-and amino-acids in addition to monoterpenoids. The last class of compounds is the most accessible for this series and is especially convenient for the synthesis of molecules with a branched C skeleton, primarily isoprenoid pheromones.Oxidative methods of transforming monoterpenoids are the most convenient and widely used methods for carrying out various transformations of starting molecules and introducing most known functional groups. Considering this aspect, articles on the synthesis of insect pheromones that for one reason or another did not appear in previous reviews are reviewed herein. ALLYLIC OXIDATION BY SELENIUM DIOXIDEOne of the most common methods for functionalizing the C skeleton of unsaturated monoterpenoids containing an isopropylidene group is regio-and stereoselective oxidation at the allylic position, for example, by SeO 2 , of geraniol (1) and its derivatives or similar compounds. This method enables introduction into molecules of hydroxy-or oxo-functions that can be used in further transformations.For example, treatment of geranylacetate (2) with a stoichiometric or catalytic (with t-BuOOH) amount of SeO 2 followed by hydride reduction gives unsaturated hydroxyacetate 3, which is widely used to synthesize insect pheromones [16][17][18][19].In particular, 3 was oxidized to aldehyde 4, which was then converted to the olefin by n-propylidenephosphorane [16], to prepare racemic 5,9-dimethylheptadecane (7), the sex pheromone of the pear leaf blister moth (Leucoptera scitella Zeller). Organocuprate coupling of the resulting allylic acetate 5 with n-hexylmagnesium bromide led to 5,9-dimethyl-3,5,9-heptadecatriene (6), exhaustive hydrogenation of which gave the desired pheromone 7.Condensation of bromoacetate 8 wth sodium malonic ester was used [17] to synthesize 10-hydroxy-4,8-dimethyl-4E,8E-decadienoic acid (11), an acyclic precursor of ferrulactone I (12), which is the principal component of the aggregation pheromone of the rusty grain beetle (Cryptolestes ferrugineus Stephen). Decarboxylation of the resulting triester 9 and subsequent saponification gave the key hydroxyacid 11, lactonization of which by bis-(4-t-butyl-N-isopropylimidazol-2-yl)disulfide gave the desired 12.

show abstract

Insect pheromones and their analogs

Cited by 2 publications

References 11 publications

Chemistry of the pheromones of mealybug and scale insects

Chemistry of the pheromones of mealybug and scale insects

Insect Pheromones Synthesized by Oxidative Transformations of Natural Monoterpenoids

Contact Info

Product

Resources

About