Identification and Assignment of the Absolute Configuration of Biologically Active Methyl-Branched Ketones from Limnephilid Caddis Flies

Bergmann, Jan; Löfstedt, Christer; Иванов, В. Д.; Francke, Wittko

doi:10.1002/1099-0690(200108)2001:16<3175::aid-ejoc3175>3.0.co;2-4

Cited by 26 publications

(19 citation statements)

References 10 publications

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“…The corresponding Grignard reagent of 1-bromo-2-methylpentane (15) [39], which was synthesized from 2-methyl-1-pentanol (14), was coupled with acetal 13 by using lithium tetrachlorocuprate (Li 2 CuCl 4 ) [40] to give 2-(8-methylundecyloxy)-tetrahydro-2H-pyran (16). The corresponding Grignard reagent of 1-bromo-2-methylpentane (15) [39], which was synthesized from 2-methyl-1-pentanol (14), was coupled with acetal 13 by using lithium tetrachlorocuprate (Li 2 CuCl 4 ) [40] to give 2-(8-methylundecyloxy)-tetrahydro-2H-pyran (16).…”

Section: Synthesis Of Estersmentioning

confidence: 99%

“…For the synthesis of ester C, 1,6-hexanediol (11) was converted into 6-bromohexan-1-ol (12) by using HBr, which was protected with 3,4-dihydropyran to form compound 13 (Scheme 4). The corresponding Grignard reagent of 1-bromo-2-methylpentane (15) [39], which was synthesized from 2-methyl-1-pentanol (14), was coupled with acetal 13 by using lithium tetrachlorocuprate (Li 2 CuCl 4 ) [40] to give 2-(8-methylundecyloxy)-tetrahydro-2H-pyran (16). Deprotection by TsOH in MeOH furnished 8-methylundecan-1-ol (17), which was converted into methyl 8-methylundecanoate (18) in one step using trichloroisocyanuric acid [41].…”

Section: Synthesis Of Estersmentioning

confidence: 99%

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Identification and Synthesis of Branched Wax‐type Esters, Novel Surface Lipids from the Spider Argyrodes elevatus (Araneae: Theridiidae)

Chinta

Goller

Uhl³

et al. 2016

Chemistry & Biodiversity

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The analysis of cuticular extracts from the kleptoparasitic spider Argyrodes elevatus revealed the presence of unusual esters, new for arthropods. These novel compounds proved to be methyl-branched long-chain fatty acid esters with methyl branches located either close or remote from the internally located ester group. The GC/MS analysis of the prosoma lipid blend from the male cuticle contained one major component, undecyl 2-methyltridecanoate (1). In contrast, four major wax-type esters, 2-methylundecyl 2,8-dimethylundecanoate (2), 2,8-dimethylundecyl 2,8-dimethylundecanoate (3), heptadecyl 4-methylheptanoate (4), and 14-methylheptadecyl 4-methylheptanoate (5), were identified in the lipid blend of female prosomata. Structure assignments were based on mass spectra, gas chromatographic retention indices, and microderivatization. Unambiguous proof of postulated structures was ensured by an independent synthesis of all five esters. Preferentially, odd-numbered carbon chains pointed to a distinct biosynthetic pathway, different from that of common fatty acids, because one or two C starter units are incorporated during the biosynthesis of all acid and alcohol building blocks present in the five esters. The striking sexual dimorphism together with the unique biosynthesis points to a function of the esters in chemical communication of the spiders, although no behavioral data are currently available to test this assumption.

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Section: Synthesis Of Estersmentioning

confidence: 99%

Section: Synthesis Of Estersmentioning

confidence: 99%

Identification and Synthesis of Branched Wax‐type Esters, Novel Surface Lipids from the Spider Argyrodes elevatus (Araneae: Theridiidae)

Chinta

Goller

Uhl³

et al. 2016

Chemistry & Biodiversity

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“…Tóth et al (1995) found that female Nepticulidae attracted males with substances similar to those isolated from the sternum V glands in Eriocraniidae and various Trichoptera (e.g. Löfstedt et al 1994;Zhu et al 1995;Kozlov et al 1996;Bergmann et al 2001Bergmann et al , 2002. However, Tóth et al (1995) did not link the pheromone production to a specific body part.…”

Section: Functionmentioning

confidence: 96%

“…The sternum V gland's general function is pheromone production, more specifically production of sex pheromones in females (Wood and Resh 1984;Resh and Wood 1985;Solem 1985;Löfstedt et al 1994;Zhu et al 1995;Bjostad et al 1996;Jewett et al 1996;Kozlov et al 1996;Bergmann et al 2001Bergmann et al , 2002. In Lepidoptera, the function of the sternum V gland is only directly known in some Eriocraniidae in which females use it to attract males (Zhu et al 1995;Kozlov et al 1996).…”

Section: Functionmentioning

confidence: 99%

“…The best known function of the sternum V gland is production of female sex pheromones (Wood and Resh 1984;Resh and Wood 1985;Solem 1985;Löfstedt et al 1994;Zhu et al 1995;Bjostad et al 1996;Jewett et al 1996;Kozlov et al 1996;Bergmann et al 2001Bergmann et al , 2002, but this does not explain the function of the sternum V gland in the males. Based on the presence of the sternum V gland in both sexes, several authors have suggested a defensive function for the gland (Eltringham 1934;Kristensen 1972Kristensen , 1984Davis 1975Davis , 1978Kozlov and Zvereva 1999).…”

Section: Functional Considerationsmentioning

confidence: 99%

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The sternum V glands in Lepidoptera

Djernæs¹

2011

Acta Zoologica

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Djernæs, M. 2011. The sternum V glands in Lepidoptera. —Acta Zoologica (Stockholm) 00: 1–16. Abstract I investigated representatives for all lepidopteran families known to possess the sternum V glands (Micropterigidae, Agathiphagidae, Heterobathmiidae, Erio‐craniidae and Lophocoronidae) as well as representatives for the two families (Neopseustidae and Nepticulidae) known to posses fenestrae on sternum IV, structures associated with the sternum V glands in Eriocraniidae. I found significant variation in the gland structure. The gland opening is associated with a variety of cuticular modifications, several of which provide enlarged evaporative surfaces for enhanced dispersal of gland products. The gland reservoir was surrounded by musculature in all families except Agathiphagidae and Nepticulidae, providing means of rapid expulsion of gland products. The fenestra in female Eriocraniidae, Neopseustidae and Nepticulidae are perforated. Furthermore, the fenestra in female Neopseustidae and Nepticulidae are associated with what appears to be functional sternum V glands consisting of a reservoir and secretory tissue albeit without a gland duct. I discuss the evolutionary history and functional considerations of the sternum V gland in Lepidoptera.

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Iridium‐Catalyzed Asymmetric Hydrogenation of Unfunctionalized, Trialkyl‐Substituted Olefins

Wang

Fraga

Hörmann

et al. 2010

Chemistry An Asian Journal

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Chiral iridium complexes with bicyclic pyridine-based N,P ligands have emerged as efficient catalysts for the enantioselective hydrogenation of unfunctionalized trialkyl-substituted olefins. Optimization of the reaction conditions by variation of the solvent, pressure, and temperature led to enantiomeric excesses of up to 99%. Three pure alkenes, (E)-2-cyclohexyl-2-butene and (E)- and (Z)-3,4-dimethyl-2-pentene were converted into the corresponding chiral alkanes with 97%, 94%, and 93% ee, respectively. Hydrogenation of the three C=C bonds of both α- and γ-tocotrienyl acetate led to α- and γ-tocopheryl acetate with very high diastereoselectivity. The same catalysts were successfully applied in the hydrogenation of trisubstituted alkenes with a carboxylic ester or a keto group in the γ position. This reaction was used as a key step in a highly enantioselective synthesis of the pheromone of the caddisfly Hesperophylax occidentalis. The hydrogenation of a structurally analogous allylic alcohol also gave high enantioselectivities.

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Identification and Assignment of the Absolute Configuration of Biologically Active Methyl-Branched Ketones from Limnephilid Caddis Flies

Cited by 26 publications

References 10 publications

Identification and Synthesis of Branched Wax‐type Esters, Novel Surface Lipids from the Spider Argyrodes elevatus (Araneae: Theridiidae)

Identification and Synthesis of Branched Wax‐type Esters, Novel Surface Lipids from the Spider Argyrodes elevatus (Araneae: Theridiidae)

The sternum V glands in Lepidoptera

Iridium‐Catalyzed Asymmetric Hydrogenation of Unfunctionalized, Trialkyl‐Substituted Olefins

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