Research Progress on the Syntheses of Chiral Methyl-Branched Aliphatic Hydrocarbons Insect Pheromones

doi:10.6023/cjoc202103007

Abstract

The chiral methyl-branched aliphatic hydrocarbon insect pheromones including single, double and multichiral methyl-branched insect pheromones are the most promising green control ofScoliopteryx libatrix,Monochamus titillator,Lyonetia clerkellaand other many pests. The syntheses of single chiral methyl-branched pheromones are reviewed according to the methods of constructing chiral methyl, whereas the preparation of double chiral methyl-branched and multichiral methyl-branched ones are illustrated on the basis of the linking strategies of the key fragments. Moreover, the advantages and disadvantages of the synthetic approaches are discussed, as well as the prospects for the synthesis of chiral methyl-branched aliphatic hydrocarbon insect pheromones.

Key words: chiral methyl, insect pheromone, asymmetric synthesis, linking strategies, progress

Cite this article

Gucheng Yuan, Qinghua Bian, Min Wang, Jiangchun Zhong. Research Progress on the Syntheses of Chiral Methyl-Branched Aliphatic Hydrocarbons Insect Pheromones[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2571-2586.

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Fig. & Tab. 23

Figure 1. Single chiral methyl-branched hydrocarbon insect pheromones

Scheme 1. Synthesis of insect pheromone 1

Scheme 2. Synthesis of insect pheromone 2

Scheme 3. Synthesis of insect pheromone 3

Scheme 4. Asymmetric catalytic synthesis of insect pheromone 4

Scheme 5. Synthesis of insect pheromone 4 via chemical resolution

Scheme 6. Synthesis of insect pheromone 5

Scheme 7. Synthesis of insect pheromone 6

Figure 2. Double chiral methyl-branched hydrocarbon insect pheromones

Scheme 8. Synthesis of insect pheromone 46 via Wittig coupling

Scheme 9. Synthesis of insect pheromone 47

Scheme 10. Synthesis of insect pheromone 49

Scheme 11. Synthesis of insect pheromone 48 via the alkylation of sulfone

Scheme 12. Synthesis of insect pheromone 50

Scheme 13. Synthesis of insect pheromone 51

Scheme 14. Synthesis of insect pheromone 46 via the addition of organic lithium to aldehyde

Scheme 15. Synthesis of insect pheromone 47 via the alkylation of TosMIC

Scheme 16. Synthesis of insect pheromone 48 via the asymmetric addition of cyclic enone

Scheme 17. Synthesis of insect pheromone 46 from chiral source

Figure 3. Poly chiral methyl-branched hydrocarbon insect pheromones

Scheme 18. Synthesis of insect pheromone 143

Scheme 19. Synthesis of insect pheromone 144 via Wittig reaction

Scheme 20. Synthesis of insect pheromone 144 via the substitution of Grignard reagent

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