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Synthese eines neuen Norpatchoulenolanalogons

Synthesis of a new analogue of norpatchoulenol

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

The synthesis of racemic 4,11,11-trimethyltricyclo[5.3.1.05,8]undec-4-en-7-ol (4), a new analogue of norpatchoulenol is described. ByDiels-Alder reaction of 6,6-dimethylcyclohexadienone (3) with methylvinyl ketone followed by hydrogenation and epimerization thesyn-diketone7 was obtained which then has been subjected to aGrignard reaction with vinyl magnesium bromide. After protection of the hydroxyl group of the resulting ketol8 the ketoether9 could be cyclisized to4 by means of a lithium suspension in refluxingTHF.4 shows a weak, characteristic odour of patchouli.

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Authors and Affiliations

  1. Institut für Pharmazeutische Chemie, Universität Wien, A-1090, Wien, Österreich

    Helmut Spreitzer, Alfred Hausensteiner & Gerhard Buchbauer

Authors
  1. Helmut Spreitzer
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  2. Alfred Hausensteiner
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  3. Gerhard Buchbauer
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Herrn Prof. Dr.C. H. Eugster mit den besten Wünschen zum 65. Geburtstag gewidmet.

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Spreitzer, H., Hausensteiner, A. & Buchbauer, G. Synthese eines neuen Norpatchoulenolanalogons. Monatsh Chem 117, 1405–1412 (1986). https://doi.org/10.1007/BF00810750

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  • DOI: https://doi.org/10.1007/BF00810750

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