The synthesis of insect sex phermones

Henrick, Clive A.

doi:10.1016/0040-4020(77)80372-4

Cited by 309 publications

(43 citation statements)

References 368 publications

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“…[4]. Monobromination of 1,7-heptanediol(13) was achieved in 72% yield by continuously extracting a mixture of diol 13 and aqueous hydrobromic acid with heptane (15). The hydroxyl group of bromide 14 was protected as its tert-butyldimethylsilyl ether (16) to give bromide 8 in 82% yield.…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of analogues of ionomycin

Hu¹,

Weller²

1994

Can. J. Chem.

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THOMAS Q. HU and LARRY WEUER. Can. J. Chem. 72, 1500Chem. 72, (1994.Based on the analysis of the crystal structure of the ~a ' + salt of ionomycin and the chemical and physical data on ionomycin, a number of ionomycin analogues have been synthesized to study the structural features affecting the Ca'+ binding and transport. Compounds 2,3, and 4 were synthesized to study the effect of additional intramolecular oxygen coordination sites on ~a ' + transport. Compounds 5a-Sd were prepared to study the effect of lipid solubility on ~a ' + binding aild transport. Compounds 6ri-6c were prepared to study the effect of the distance between the P-diketone and the carboxyl group on ~a ' + transport. A general synthetic route to these compounds has been developed. The key reactions in this route are the consecutive legioselective alkylations of the dianion of 2,4-pentanedione with the appropriate bromides.

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Section: Resultsmentioning

confidence: 99%

Design and synthesis of analogues of ionomycin

Hu¹,

Weller²

1994

Can. J. Chem.

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“…An examination of these reviews will produce some insight into the strategies that were, and still are, being em- Katzenellenbogen (1977) Henrick (1977) Rossi (1978a) Brand et al (1979) Bestmann and Vostrowsky (1979) Smith and Williams (1979) Henrick et al (1982) ployed in synthesizing pheromones. This chapter, therefore, is written with several additional purposes in mind.…”

Section: Introductionmentioning

confidence: 99%

Tabulations of Selected Methods of Syntheses That Are Frequently Employed for Insect Sex Pheromones, Emphasizing the Literature of 1977–1982

Sonnet

1984

Techniques in Pheromone Research

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“…Our future goal is a pilot plant scale. Classical methods to carry out the synthe sis of compounds like E-9-dodecen-l-yl acetate are the acetylenic route [2] and the Wittig reaction [3]. The first one seems to be the best suited for largescale synthesis, however, in order to achieve very high yields, hexamethylphosphoryltriamide must be used as a co-solvent.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of E-9-Dodecen-1-yl Acetate Using Organomanganese Reagents

Belmar

Tellez

Baeza

et al. 2000

Zeitschrift Für Naturforschung B

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Pheromone, Organomanganese, E-9-Dodecen-l-yl Acetate The Grignard reagent obtained from 2-(6-bromohexyloxy)-tetrahydropyrane, by treatment with anhydrous manganese(II) chloride was transformed to the corresponding organomanganese reagent, which was coupled with E-l-bromo-3-hexeneby treatment with anhydrous manganese chloride. Further deprotection and acetylation furnished E-9-dodecen-l-yl acetate. A second procedure involved the coupling of E-3-hexenylmanganese bromide and 6-bromohexyl acetate. Coupling reactions were carried out at 0 C, using as co-solvent.

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The synthesis of insect sex phermones

Cited by 309 publications

References 368 publications

Design and synthesis of analogues of ionomycin

Design and synthesis of analogues of ionomycin

Tabulations of Selected Methods of Syntheses That Are Frequently Employed for Insect Sex Pheromones, Emphasizing the Literature of 1977–1982

Synthesis of E-9-Dodecen-1-yl Acetate Using Organomanganese Reagents

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