Monatshefte fur Chemie p. 1345 - 1358 (1985)
Update date:2022-08-24
Topics:
Buchbauer, Gerhard
Heneis, Vera M.
Krejci, Viktoria
Talsky, Claudia
Wunderer, Hanneliese
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 an all-trans-connection of the three rings.Periodate cleavage of 12 leads to 13 which can be transformed into the triester 14 by Baeyer-Villiger oxidation.The configuration of the aldehyde group in 13 as well of the formyloxy group in 14 has been ensured to be equatorial.LAH-reduction of 14 leads to the triol 16 which after cyclisation and reductive dehydroxylation furnishes the fragrance compound 4. - 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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