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Pheromones of Pine Sawflies: Synthesis of a Pure (2S,3R)-3-Methylalkan-2-ol Stereoisomer via an Asymmetric 1,3-Dipolar Cycloaddition; Preparation of a Pheromone Component of Macrodiprion nemoralis
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
2000 (English)In: Synthesis, ISSN 0039-7881, Vol. 2000, no 13, 1863-1867 p.Article in journal (Refereed) Published
Abstract [en]

This paper presents a new approach to the preparation of enantiomerically pure (2S,3R)-3-methylalkan-2-ols, the esters of which are sex pheromones of several pine sawflies. Thus, an asymmetric 1,3-dipolar cycloaddition between a sulfur containing 1,3-dipole and a dipolarophile attached to (1R)-camphorsultam containing a vinyl ether functionality furnished a 90:10 diastereomeric mixture of trans-3,4-disubstituted tetrahydrothiophene amides. The major one was converted to an enantiomerically pure tetrahydrothienylmethyl bromide, which was coupled with a monoalkylated dithiane unit. After Raney nickel reduction (2S,3R,7R,9S)-3,7,9-trimethyltridecan-2-ol was obtained, the acetate of which is the attractant sex pheromone component of Macrodiprion nemoralis. Because this new approach is quite efficient it can be valuable for the synthesis of similar compounds.

Place, publisher, year, edition, pages
2000. Vol. 2000, no 13, 1863-1867 p.
Keyword [en]
Pheromone Synthesis
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-1815DOI: 10.1055/s-2000-8221ISI: 000165394500013Scopus ID: 2-s2.0-0033693940Local ID: 1858OAI: oai:DiVA.org:miun-1815DiVA: diva2:26847
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-10-08Bibliographically approved

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Karlsson, StaffanHögberg, Hans-Erik
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CiteExportLink to record
Permanent link

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Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
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More styles
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  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
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  • Other locale
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  • asciidoc
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