Synthesis of ?-neryl and ?-geranyl propionates ? Components of the sex pheromone of San Jose scale

Moiseenkov, A. M.; Ishchenko, R. I.; Веселовский, В. В.; Odinokov, V. N.; Полунин, Е. В.; Kovalev, B. G.; Cheskis, B. A.; Толстиков, Г. А.

doi:10.1007/bf00597723

Cited by 3 publications

(3 citation statements)

References 8 publications

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“…13 In another synthesis of the two isomers using synthons with preset stereochemistry, Moiseenkov and coworkers alkylated 1iodo-3-methyl-3-butene with an allylic (E)-hydroxysulfone or a related (Z)-hydroxysulfonamide, but because the preparation of these two synthons was not described, the overall utility of the syntheses is not clear. 18 A related scheme formed the carbon skeleton by sequential alkylation of bis(arylsulphonyl)methane with (E-Z)-4-chloro-3-methyl-2-buten-1-ol and ethyl 2-methylprop-2-en-1-yl carbonate but suffered from low overall yield and incomplete control of the alkene stereochemistry. 19 A 12-step synthesis of a mixture of the two isomers starting from methyl 4-oxopentanoate is mentioned only for completeness.…”

Section: Overview Of Scale and Mealybug Pheromonesmentioning

confidence: 99%

Chemistry of the pheromones of mealybug and scale insects

Zou

Millar

2015

Nat. Prod. Rep.

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Section: Overview Of Scale and Mealybug Pheromonesmentioning

confidence: 99%

Chemistry of the pheromones of mealybug and scale insects

Zou

Millar

2015

Nat. Prod. Rep.

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“…Lithiated d-hydroxyallylic or saturated sulfones (including those containing a chiral centre) and the corresponding unsaturated terpenoid halides served as the starting compounds. This methodology was used for the preparation not only of relatively small molecules [for example, the pheromone components of San-Jose scale, viz., a-neryl and a-geranyl propionates (13a,b) 67 ], but also of long-chain natural regulators, such as polyprenol-and dolichollike alcohols 14 68 or 15. 69 The addition of a crown ether, viz., dibenzo-18-crown-6 (DB-18-C-6), to a solution of sodium in liquid ammonia in the stage of reductive desulfonation made it possible to suppress the undesirable allylic isomerisation of the adjacent C=C bond.…”

Section: Syntheses Based On Amentioning

confidence: 99%

Sulfones and sulfoxides in the total synthesis of biologically active natural compounds

Prilezhaeva¹

2000

Russ. Chem. Rev.

185

103

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A graphical treatment of the tone reproduction problem in television systems satisfactorily answered by extensive experimental work, using the techniques of subjective appraisal which have been increasingly developed in recent years. Direct comparison of a reproduction and an original, with all the parameters of the system accurately known, calls, of course, for a considerable experimental effort. Such limited observations as have been made, however, suggest that the shape of the curves at least gives a good impression of the relative effects of viewing cathode-ray tubes with different values of A, and operating under, different conditions. It is not intended to draw any conclusions or express any as to what form of reproduction characteristic is most desirable. There can, however, be little doubt that there are instances where faithful reproduction is not desirable -where, in fact, the television system can improve on the eye and convey the maximum of information or enhance the asthetic value of a scene by emphasizing certain luminosity differences at the expense of others. To a large extent the value of such distortions must be a matter of personal preference.What constitutes the most desirable form of characteristic is, again, a question which calls for large-scale experiment on a subjective basis; factors such as signal-to-noise ratio and the effect of the characteristic on apparent definition have to be taken into account.Reference may be made in passing to the results of Jones's investigation into the preferences of a large number of observers in the matter of photographic prints.Q) This investigation tends to show that preferred prints are those in which the gradient of the logL,/logL, curve is approximately unity for the medium tones, and that a greater fall in the gradient is acceptable towards black. It would be unwise to assume, however, that the results obtained are necessarily applicable to television practice, where the form of the transfer characteristics and the viewing conditions are different. One general principle which does not seem to be in dispute is that, whereas a considerable tolerance exists when the reproduction is in monochrome, colour calls for a much closer approach to fidelity in luminosity reproduction.Large-area luminance range in modern aluminized cathoderay tubes, in the absence of external light, appears to offer little scope for worth-while improvement. It is worth noting, however, that the importance of good detail luminance range in determining the subjective quality of television pictures has been stressed by Law@) and other writers.Assuming that an optimum characteristic, or range of characteristics, can be defined, practical realization of the optimum raises a number of issues, e.g. the relative contributions of the transmitting and receiving apparatus to the overall result, and whether the desired objective can best be arrived at by selection of the camera or cathode-ray tube characteristic or by suitable circuit design.It is hoped that the present communication may help...

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“…Moiseenkov et al 88 synthesised the propionate (Z)-177 starting from isoprenoid (Z)-hydroxy sulfonamide 185. 89 The synthetic scheme involved alkylation of the sulfonamide 185 with 3-methylbut-3-enyl iodide 186 to form sulfonamide 187 and reductive desulfation of the latter in the presence of dibenzo-18crown-6 (DB-18-C-6).…”

Section: Sex Pheromone Of the San Jose Scalementioning

confidence: 99%

Synthesis of insect pheromones belonging to the group of (Z)-trisubstituted alkenes

Grigorieva¹,

Tsiklauri²

2000

Russ. Chem. Rev.

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Stereo-and regiocontrolled methods for the construc-Stereo-and regiocontrolled methods for the construction of a ( tion of a (Z Z)-trisubstituted C=C bond and for the regiospecific )-trisubstituted C=C bond and for the regiospecific introduction of a chiral fragment are exemplified in total syntheses introduction of a chiral fragment are exemplified in total syntheses of insect pheromones belonging to ( of insect pheromones belonging to (Z Z)-trisubstituted alkenes. The )-trisubstituted alkenes. The bibliography includes 113 references bibliography includes 113 references. .

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Synthesis of ?-neryl and ?-geranyl propionates ? Components of the sex pheromone of San Jose scale

Cited by 3 publications

References 8 publications

Chemistry of the pheromones of mealybug and scale insects

Chemistry of the pheromones of mealybug and scale insects

Sulfones and sulfoxides in the total synthesis of biologically active natural compounds

Synthesis of insect pheromones belonging to the group of (Z)-trisubstituted alkenes

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