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Convenient Method for the Synthesis of Lineatin, a Pheromone Component of Trypodendron-Lineatum
KTH, Sweden.
KTH, Sweden.
KTH, Sweden.ORCID iD: 0000-0001-7158-6393
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1991 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 56, no 10, 3358-3362 p.Article in journal (Refereed) Published
Abstract [en]

Synthesis of racemic lineatin (1), a pheromone component of Trypodendron lineatum, is described. Condensation of 5-methyl-5-hexen-2-one (2) and triethyl phosphonoacetate with LiN(SiMe3)2 gave esters 3, which upon hydrolysis gave acids 4a-f. The bicyclo[3.2.0] ring compounds 5 and 6 were obtained via an intramolecular [2 + 2] addition by refluxing underivatized carboxylic acids 4a-f with NaOAc and Ac2O. Compound 5 was isomerized to the thermodynamically more stable isomer 6 using a Pd/C catalyst activated with hydrogen. Reduction of 6 with LiAlH4 gave the endo and exo isomers 7a and 7b (4:1). Isolation of the alcohol 7a followed by acetylation gave 8. Subsequent oxidation with OsO4 and methylmorpholine N-oxide gave diol 9. Cleavage of 9 with H5IO6 in diethyl ether gave keto aldehyde 10, which was converted to keto acetal 11. Treatment of 11 with MeMgBr followed by acidic workup gave 1. The overall efficiency is approximately 20%.

Place, publisher, year, edition, pages
1991. Vol. 56, no 10, 3358-3362 p.
Keyword [en]
aggregation pheromone, cyclo-addition, absolute-configuration, scolytidae, coleoptera, olivier, alkenes, (+/-)-lineatin, rearrangements, (+)-lineatin
National Category
Natural Sciences
Research subject
Natural Science, Organic Chemistry; Natural Science, Ecological chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-14098ISI: A1991FL74400033OAI: oai:DiVA.org:lnu-14098DiVA: diva2:440822
Note

Fl744 Times Cited:13 Cited References Count:33

Available from: 2011-09-13 Created: 2011-09-13 Last updated: 2017-01-11Bibliographically approved

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CiteExportLink to record
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Citation style
  • apa
  • harvard1
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