Pheromones, sex

The Afncan dwarf crocodile secretes a volatile substance believed to be a sex pheromone It IS a mixture of two stereoisomers one of which is shown... 

Ethyl cinnamate (one of the constituents of the sex pheromone of the male onental fmit moth)... 

Z) 5 Tetradecen 4 olide (sex pheromone of female Japanese beetle)... 

Slow release formulations incorporate nonpersistent compounds, eg, methyl parathion, insect growth regulators, and sex pheromones, in a variety of granular, laminated, microencapsulated, and hoUow-ftber preparations. 

Z)-3-Decaioic acid (the sex pheromone of the fumituie carpet beetle)... 

Z)-9-Tricosene [(Z)-CH3(CH2)7CH=CH(CH2)i2CH3] is the sex pheromone of the female housefly. Synthetic (Z)-9-tricosene is used as bait to lure male flies to traps that contain insecticide. Using acetylene and alcohols of your choice as starting materials, along with any necessary inorganic reagents, show how you could prepare (Z)-9-tricosene. 

The preparation of the sex pheromone of the bollworm moth, ( )-9,ll-dodecadien-l-yl acetate, from compound A has been described. Suggest suitable reagents for each step in this sequence. 

Fucoserraten, ectocarpen, and multifidene are sex pheromones produced by marine brown algae. What are their systematic names (The latter two are a bit difficult make your best guess.)... 

Named bombykol, the sex pheromone secreted by the female silkworm moth has the formula C16H280 and the systematic name (10 ,12Z)-10,12-hexa-decadien-l-oJ. Draw bombykol showing correct geometry for the two double bonds. 

In 1952, it was reported that a constituent of excretions from female American cockroaches of the species Periplaneta ameri-cana is an extraordinarily potent sex pheromone.1 Early attempts to isolate and characterize the active compounds were hampered because individual cockroaches store only minute amounts of the pheromone ( 1 pg), and a full 25 years elapsed before Persoons et al. reported the isolation of two extremely active compounds, periplanones A and B.2 The latter substance is present in larger relative measure and its germacranoid structure (1, without stereochemistry) was tentatively assigned on the basis of spectroscopic data. Thus, in 1976, the constitution of periplanone B was known but there remained a stereochemical problem of a rather serious nature. Roughly three years intervened between the report of the gross structure of periplanone B and the first total synthesis of this substance by W. C. Still at Columbia.3... 

Based on the successful series of transformations summarized in Scheme 1, Schreiber and Santini developed an efficient and elegant synthesis of periplanone B (1),8 the potent sex pheromone of the American cockroach, Periplaneta americana. This work constitutes the second total synthesis of periplanone B, and it was reported approximately five years after the landmark periplanone B synthesis by W.C. Still9 (see Chapter 13). As in the first synthesis by Still, Schreiber s approach to periplanone B takes full advantage of the facility with which functionalized 5-cyclodecen-l-one systems can be constructed via anionic oxy-Cope rearrangements of readily available divinylcyclohexanols.5 7 In addition, both syntheses of periplanone B masterfully use the conformational preferences of cyclo-decanoid frameworks to control the stereo- and regiochemical course of reactions carried out on the periphery of such ring systems.10... 

In addition to the synthetic applications related to the stereoselective or stereospecific syntheses of various systems, especially natural products, described in the previous subsection, a number of general synthetic uses of the reversible [2,3]-sigmatropic rearrangement of allylic sulfoxides are presented below. Several investigators110-113 have employed the allylic sulfenate-to-sulfoxide equilibrium in combination with the syn elimination of the latter as a method for the synthesis of conjugated dienes. For example, Reich and coworkers110,111 have reported a detailed study on the conversion of allylic alcohols to 1,3-dienes by sequential sulfenate sulfoxide rearrangement and syn elimination of the sulfoxide. This method of mild and efficient 1,4-dehydration of allylic alcohols has also been shown to proceed with overall cis stereochemistry in cyclic systems, as illustrated by equation 25. The reaction of trans-46 proceeds almost instantaneously at room temperature, while that of the cis-alcohol is much slower. This method has been subsequently applied for the synthesis of several natural products, such as the stereoselective transformation of the allylic alcohol 48 into the sex pheromone of the Red Bollworm Moth (49)112 and the conversion of isocodeine (50) into 6-demethoxythebaine (51)113. 

For trisubstituted olefins, the nucleophile attacks predominantly at the less substituted end of the allyl moiety, e.g. to afford a 78 22 mixture of 13 and 14 (equation 7). Both the oxidative addition of palladium(O) and the subsequent nucleophilic attack occur with inversion of configuration to give the product of net retention7. The synthesis of the sex pheromone 15 of the Monarch butterfly has been accomplished by using bis[bis(l,2-diphenylphosphinoethane)]palladium as a catalyst as outlined in equation 87. A substitution of an allyl sulfone 16 by a stabilized carbon nucleophile, such as an alkynyl or vinyl system, proceeds regioselectively in the presence of a Lewis acid (equation 9)8. The... 

Behavioral and Hormonal Chemicals. Sex pheromones, which attract pests to traps, are used effectively to control some insect pests, like the grape berry moth (46) and cabbage looper. With other Insect pests, sex pheromones have been effectively used to monitor the size of pest insect populations to determine when pesticide treatments should be made. 

Hong, W.S., Chen, S.X., and Zhang, Q.Y. et al. (2006). Sex organ extracts and artihcial hormonal compounds as sex pheromones to attract broodfish and to induce spawning of Chinese black sleeper (Bostrichthys sinensis Lacepede). Aquaculture Research 37, 529-534. 

Albrecht M (2004) Supramolecular Templating in the Formation of Helicates. 248 105-139 Ando T, Inomata S-I, Yamamoto M (2004) Lepidopteran Sex Pheromones. 239 51-96 Angyal SJ (2001) The Lobry de Bruyn-Alberda van Ekenstein Transformation and Related Reactions. 215 1-14... 

Consider general approaches to the synthesis of (22), the sex pheromone of the olive fly, a serious pest of... 

Adams M., Teeter J.H., Katz Y. and Johnsen P.B. (1987). Sex pheromones of the sea lamprey steroid studies on urinary products. J Chem Ecol 13, 387-395. 

Dizinno G., Whitney G. and Nyby J. (1978). Ultrasonic vocalisation by male mice (Mus musculus) to female sex pheromone experiential determinants. Behav Biol 22, 104-113. 

Dulka J. (1993). Sex pheromone systems in goldfish comparable to vomeronasal systems in Tetrapods Brain Behav Evol. 42, 265-280. 

Hanson L., Sorensen P. and Cohen Y. (1998). Sex pheromones and amino acids evoke distinctly different spatial patterns of electrical activity in the goldfish olfactory bulb. Ann NY Acad Sci 855, 521-524. 

Hatanaka T. (1991). Is the mouse vomeronasal organ a sex pheromone receptor In Chemical Signals in Vertebrates 6 (Doty R.L. and Muller-Schwarze D., eds). Plenum, New York, pp. 27-30. 

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