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Structure Elucidation and Synthesis of Dioxolanes Emitted by Two Triatoma Species (Hemiptera Reduviidae)
Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
University of Hamburg.
University of Hamburg.
Fiocruz, Belo Horizonte, Brazil.
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2011 (English)In: Journal of natural products (Print), ISSN 0163-3864, E-ISSN 1520-6025, Vol. 74, no 4, 690-694 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2011. Vol. 74, no 4, 690-694 p.
Keyword [en]
chagas-disease, chemical communication, rhodnius-prolixus, esters, rearrangements, derivatives, volatiles, aldehydes, acetals, ketones
National Category
Ecology Chemical Sciences
Research subject
Natural Science, Ecological chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-14872DOI: 10.1021/np100748rISI: 000289742300023OAI: oai:DiVA.org:lnu-14872DiVA: diva2:447121
Note

753CL Times Cited:0 Cited References Count:23

Available from: 2011-10-10 Created: 2011-10-10 Last updated: 2017-01-11Bibliographically approved

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Bohman, BjörnUnelius, C. Rikard
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