Mosquito oviposition attractant

Figure 4.14. Applications of oxathianes linalool [53], dimethyl acetylcitramalate [54], mevalolactone [56], malyngolide [55], and the mosquito oviposition attractant [39]. For the latter, the C-5 stereocenter was formed by a chelate-controlled reduction while the C-6 position could be produced as either epimer by a chelate or acyclic mechanism, depending on the reducing agent.

Muricatacin 89 has been prepared from the D-isoascorbic acid-derived bis-epoxide equivalent 88 [SPR VoL26, p.l90, ref. 22] by two routes, one of which is shown in Scheme 17. Similarly, L-ascorbic acid is the starting material in a synthesis of 6-hydroxy-5-valerolactones, via the formal bis-epoxide equivalent 90, epimeric with 88, converted to epoxide 91 (with epoxide transposition), and thence to lactone 92, the major mosquito oviposition attractant pheremone (Scheme 18). ... 

Scheme 41 summarizes Couladouros s synthesis of the oviposition attractant pheromone of the Southern house mosquito (Culexpipiensfatigans)y (5R,6S)-6-acetoxy-5-hexadecanolide (28) [66]. The key-steps are (i) -selective Schlosser olefination (A B), asymmetric dihydroxylation (B C), and lactonization of carbonate C to the desired 6-lactone with inversion at C-5. 

Based on the previous work of this group on the three-component aza[4+2]/ allylboration strategy to construct polysubstituted piperidines [62], Gao and Hall developed a catalytic enantioselective version [63] of the corresponding oxygeneous process to construct a-hydroxyalkylated pyrans from 3-boronoacrolein [64], This recent variant of a Vaultier-Lallemand one-pot three-component reaction (see Scheme 12.14) was successfully applied to a concise total synthesis of (5R,6S)-6-acetoxy-5-hexadecanolide 128 (Scheme 12.20), the oviposition attractant pheromone of the female Culex mosquito [65] capable of transmitting the West Nile virus. 

An egg parasitoid uses the sex pheromone of the tussock moth to find the eggs, which are deposited shortly after mating.168 An oviposition attractant for the mosquito, Culexpipiens fatigans, is shown (11.38).169... 

Ikeshoji T. 1975. Chemical analysis of wood creosote for species-specific attraction of mosquito oviposition. Appl Ent Zool 10(4) 302-308. 

The enantiospecific synthesis of ( + )-ef7r/zro-(5 S, 6i )-6-acetoxy-5-hexadecanolide (475), an optically active form of the major component of an oviposition attractant pheromone of the mosquito Culexpipiens fatigans, exploits the 6,8-dioxabicyclo[3.2.1]octane system to provide... 

A methodologically similar approach was successfully utilized independently for the synthesis of the oviposition attractant pheromone of the female Culex mosquito (—)-(5/ ,6S )-6-acetoxyhexadecanolide (28), by Kotsuki et al. 45) and Li et al. 46). While the Li group carried out a direct aldol reaction between undecanal (23) and cyclopentanone (24) to obtain the desired isomer 25 in excellent enantio- and diastereoselectivity, the Kotsuki group introduced the stereogenic centers by a reaction between 24 and the dithiane 26 under solvent-free conditions (Scheme 7). 

Turning to detritivores, several species of Culex and Aedes mosquitoes are attracted to potential oviposition sites or stimulated to oviposit by pheromones emitted by conspecific eggs, larvae, or pupae (Mulla, 1979). Presumably such pheromones indicate locales of comparatively ample resources which have proved favorable to recent development of conspecifics. On the other hand, larvae of some of these same species, when overcrowded, emit chemicals which are toxic or growth-retarding to conspecifics (Mulla, 1979). How these two facets of chemical regulation of mosquito egg and larval density relate to one another and to individual fitness is uncertain and merits further study. 

Of the simpler 8-lactone natural products, syntheses of malyngolide, mevalonolactone, and an oviposition-attractant pheromone of a mosquito ... 

J. Pelletier et al.. An odorant receptor from the southern house mosquito Culex pipiens quinquefasciatus sensitive to oviposition attractants, PLOS ONE, 5, el0090, 2010. 

Hughes, D. T., Pelletier, J., Luetje, C. W., and Leak W. S. Odorant receptor from the southern house mosquito narrowly tuned to the oviposition attractant skatole. J Chem Ecol 36, 797-800 (2010). 

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