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Structure Elucidati...
Structure Elucidation and Synthesis of Dioxolanes Emitted by Two Triatoma Species (Hemiptera Reduviidae)
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- Bohman, Björn (författare)
- Linnéuniversitetet,Institutionen för naturvetenskap, NV
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- Troger, A. (författare)
- University of Hamburg
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- Franke, S. (författare)
- University of Hamburg
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- Lorenzo, M. G. (författare)
- Fiocruz, Belo Horizonte, Brazil
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- Francke, W. (författare)
- University of Hamburg
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- Unelius, C. Rikard (författare)
- Linnéuniversitetet,Institutionen för naturvetenskap, NV
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(creator_code:org_t)
- 2011-04-12
- 2011
- Engelska.
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Ingår i: Journal of natural products (Print). - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 74:4, s. 690-694
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- Volatiles from the metastemal glands of two species Of true bugs of the Triatominae subfamily, Triatoma brasiliensis and Triatoma infestans, Were analyzed by SPME-GC/MS. Two sets of new natural products were found: (4S,5S)- and (4R,SR)-2,2,4-triethyl-5-methyl-1,3-dioxolane (1) (major component) and (45*,5S*)-2,4-diethyl-2,S-dimethyl-1,3-dioxolane (2) (trace component),-,(2R/S,4S,SS)- as well as (2R/S,4R,5R)-4-ethyl-5-methyl-2-(1-methylethyl)-1,3-dioxolane (3) (minor component), (2R/S,4S*,5S*).-4-ethyl-5-methyl-2-(1-methylpropyl)-1,3-dioxolane (4), (trace component), and (2R/S,4S*,5S*)-4-ethyl-5-methyl-2-(2-methylpropyl)-1,3-dioxolane (5) (trace component). Syntheses of optically active 1 and 3 were carried out by reacting pure,enantiomers of 2,3-pentanediol with 3-pentanone or 2-methylpropanal. The preparation of, pure 1 stereoisomers of 2,3-pentanediol involved a novel key step for the synthesis of secondary alcohols: the reduction of a carboxylic ester by means of DIBAH and in situ alkylation of the intermediate by Grignard reaction at low temperature Starting from the pure enantiomers of methyl lactate; all four stereoisoniers of 2,3-pentanediol were synthesized. and transformed, to the corresponding isomers of 1 and 2. Relative configurations of the natural products and enantiomeric compositions of naturally occurring 1 and :2 were determined by comparison of their mass spectra and gas chromatographic retention times (co-injection) I with those of authentic reference samples.
Ämnesord
- NATURVETENSKAP -- Biologi -- Ekologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences -- Ecology (hsv//eng)
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Nyckelord
- chagas-disease
- chemical communication
- rhodnius-prolixus
- esters
- rearrangements
- derivatives
- volatiles
- aldehydes
- acetals
- ketones
- Ekologisk kemi
- Ecological chemistry
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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