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Simplified isolation procedure and interconversion of the diastereomers of nepetalactone and nepetalactol
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
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2005 (English)In: Journal of natural products (Print), ISSN 0163-3864, E-ISSN 1520-6025, Vol. 68, no 6, 886-890 p.Article in journal (Refereed) Published
Abstract [en]

Three nepetalactones were isolated from Nepeta racemosa (mussinii) by traditional methods. An improved method was developed to isolate nepetalactones from N. faassenii. An epimerization procedure was used to prepare the fourth 7S-nepetalactone diastereomer. The cis-fused nepetalactols were prepared by reduction of the corresponding nepetalactones, while the trans-fused nepetalactols were unstable and found to undergo ring-opening reactions yielding iridodials. The characterizations and structural assignments by means of NMR agree with quantum chemical density functional calculations.

Place, publisher, year, edition, pages
2005. Vol. 68, no 6, 886-890 p.
Keyword [en]
APHID SEX-PHEROMONE, IDENTIFICATION, DENSITY, STEREOCHEMISTRY, EXCHANGE, CATARIA
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-37816DOI: 10.1021/np049647dISI: 000230153900012Scopus ID: 2-s2.0-22544463923OAI: oai:DiVA.org:kth-37816DiVA: diva2:435278
Note
QC 20110817Available from: 2011-08-17 Created: 2011-08-17 Last updated: 2017-12-08Bibliographically approved

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Santangelo, Ellen M.Sandell, JohanBaeckström, PeterSvensson, MatsJacobsson, Ulla
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