A New Synthesis of Desmethylambraoxide

Article abstract of DOI:10.1007/BF00811105

A new synthesis of the title compound starting from abietic acid is described.Regioselective osmylation of the Δ^13,14-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