Oviposition attractants

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. 

For species whose larvae are specialist feeders, finding suitable plants for oviposition is of great importance. Com earworm moths, Heliothis armigera, will oviposit on twine impregnated with an extract of com silk (15.). The rice stemborer, Chilo oleiadellus. female will be attracted to and oviposit near a component of rice plants identified as p-methylacetophenone (16). Some of these oviposition attractants are contact materials and, thus, are probably of no use in practical applications. This is the case for many of the butterflies of the Nymphalid family. The Indian butterfly, Papilio demoleus. seems to require some non-volatile component in citrus leaves to induce oviposition, although it seems to be attracted, at least partially, to the odor of the leaves (17.). 

While the data base of these experiments is being expanded, it should be remembered that the isolation and purification of these metabolites is no easy accomplishment and that preparative costs are prohibitive. Field tests, if they are to be carried out on native plant populations without bias, must depend on the migratory habits of virescens and since the ovipositional attractants (4and/S-DVT diols) are added as a. bolus to the resistant plant their lifetime is probably short, with oxidation occurring in the first few hours (22). 

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... 

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.

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... 

Ishikawa, Y., IkeshojI, T. Matsumoto, Y. (1978) A propylthio moiety to the oviposition attractant and stimulant of the onion fly, Hyiemya antique Meigen. Appi. Entomoi. Zooi. 13, 115-122. 

A mixture of aristolochic acids and inositol was found to be an oviposition attractant for an Aristolochiaceae-feeding swallowtail, Atrophaneura alcinous, and induced a response identical to that of the host plant (Nishida and Fukami, 1989). 

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). 

Thus, in commercial onion Helds, food sources appear to be stronger attractants of D. antiqua than oviposition attractants. 

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

Honda, H., T. Ishiwatari Y. Matsumoto. 1988. Fungal volatiles as oviposition attractants for the yellow peach moth, Congethes punctiferalis (Guenee) (Lepidoptera Pyralidae). J. Insect Physiol. 34 205-211. 

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). ... 

A. J. Mordue et al.. Behavioural and electrophysiological evaluation of oviposition attractants for Culex quinquefasciatus say (Diptera Culicidae), Experientia, 48,1109,1992. 

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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