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Über eine neue Synthese von Desmethylambraoxid

A new synthesis of desmethylambraoxide

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

Abstract

A new synthesis of the title compound starting from abietic acid is described. Regioselective osmylation of the Δ13, 14-double bond of abietic acid methyl ester (6) and subsequent hydrogenation furnishes dihydrodihydroxyabietic acid methyl ester (12) with anall-trans-connection of the three rings. Periodate cleavage of12 leads to13 which can be transformed into the triester14 byBaeyer-Villiger oxidation. The configuration of the aldehyde group in13 as well of the formyloxy group in14 has been ensured to be equatorial.LAH-reduction of14 leads to the triol16 which after cyclisation and reductive dehydroxylation furnishes the fragrance compound4.

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Authors and Affiliations

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

    Gerhard Buchbauer, Vera M. Heneis, Viktoria Krejci, Claudia Talsky & Hanneliese Wunderer

Authors
  1. Gerhard Buchbauer
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  2. Vera M. Heneis
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  3. Viktoria Krejci
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  4. Claudia Talsky
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  5. Hanneliese Wunderer
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Additional information

Herrn Prof. Dr.M. Wichtl mit den besten Wünschen zum 60. Geburtag gewidmet.

Auszugsweise vorgetragen auf der 5. wissenschaftlichen Tagung der Österreichischen Pharmazeutischen Gesellschaft am 16. April 1985 in Graz.

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Buchbauer, G., Heneis, V.M., Krejci, V. et al. Über eine neue Synthese von Desmethylambraoxid. Monatsh Chem 116, 1345–1358 (1985). https://doi.org/10.1007/BF00811105

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  • DOI: https://doi.org/10.1007/BF00811105

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