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Über eine neue Synthese von Desmethylambraoxid |
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| Authors: | Gerhard Buchbauer Vera M Heneis Viktoria Krejci Claudia Talsky Hanneliese Wunderer |
| Institution: | (1) Institut für Pharmazeutische Chemie, Universität Wien, A-1090 Wien, Österreich |
| Abstract: | A new synthesis of the title compound starting from abietic acid is described. Regioselective osmylation of the  13, 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.Auszugsweise vorgetragen auf der 5. wissenschaftlichen Tagung der Österreichischen Pharmazeutischen Gesellschaft am 16. April 1985 in Graz. |
| Keywords: | Abietic acid Ambergris fragrance compound Baeyer-Villiger oxidation Decahydro-1-naphthalene-carboxylic acid derivatives Dodecahydro-1H-naphtho[2 1-b]pyrane derivatives Periodate cleavage Reductive dehydroxylation Regioselective osmylation |
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