41747-05-1Relevant articles and documents
Formal synthesis of Ambrox and 9-epiambrox
Cortes,Armstrong,Reyes,Lopez,Madariaga
, p. 1995 - 2002 (1996)
(-)-Drimenol (5) was used as starting material for the synthesis of diastereoisomeric diols 3 and 4, through the nitrile 7. Compounds 3 and 4 are the direct precursors of Ambrox (1) and 9-epiambrox (2).
Synthesis of decalin type chiral synthons based on enzymatic functionalisation and their application to the synthesis of (-)-ambrox and (+)-zonarol
Akita, Hiroyuki,Nozawa, Masako,Shimizu, Hiroyo
, p. 1789 - 1799 (2007/10/03)
Stereoselective syntheses of (-)-ambrox 2 and (+)-zonarol 3 were achieved based on the enzymatic syntheses of (8aS)- and (8aR)-decalin-type 1,3-diols 1, respectively. Non-racemic intermediates such as (8aS)-1 and (8aR)-1 were obtained based on the enantioselective hydrolyses of the phenolic acetal derivative (±)-7 by acylase I.
The chemistry of thujone. XX. New enantioselective syntheses of Ambrox and epi-Ambrox
Kutney, James P.,Cirera, Carles
, p. 1136 - 1150 (2007/10/03)
The development of a new synthetic approach to (-)-Ambrox (37) and epi-Ambrox (29) using thujone (1) as a chiral synthon, is presented. Thujone (1), a readily available starting material obtained from Western red cedar, can be efficiently converted to β-cyperone (2) and the latter is then chemically elaborated to the key intermediate, the enone 6. A carbonyl transposition of 6 to enone 9 also allows a formal synthesis of (-)-Polywood (18).
Formal synthesis of (±)-Ambrox
Barco, Achille,Benetti, Simonetta,Bianchi, Anna,Casolari, Alberto,Guarneri, Mario,Pollini, Gian P.
, p. 8333 - 8338 (2007/10/02)
The immediate precursor of (±)-Ambrox 1 has been conveniently prepared in a seven-step sequence starting from the readily available methyl 2-oxo-5,5,8a-trimethyldecahydronaphthalene-1-carboxylate 2, in turn derived by stannic chloride-mediated cyclization of methyl 3-oxo-5-(2,6,6-trimethylcyclohexen-1-yl)pentanoate.
Ambergris compounds from labdanolic acid
Urones,Basabe,Marcos,Gonzalez,Jimenez,Sexmero,Lithgow
, p. 9991 - 9998 (2007/10/02)
Labdanolic acid (Cistus ladaniferus) is transformed into derivatives with amber odor. The strategy used allowed a process in which the oxidative decarboxylation reaction was carried out with the hydroxyl group protected.
A formal synthesis of (±)-Ambrox
Snowden,Linder
, p. 4119 - 4120 (2007/10/02)
Bicyclic diol 6, a direct precursor of (±)-Ambrox ((±)-7), has been synthesised in four steps (35% yield) from the known bicyclic enone 2.
Configuration-Odor Relationship in 5β-Ambrox
Escher, Sina,Giersch, Wolfgang,Niclass, Yvan,Bernardinelli, Gerald,Ohloff, Guenther
, p. 1935 - 1947 (2007/10/02)
The four possible A/B cis-fused diastereomers of Ambrox have been synthesized and their configurations and conformations established by X-ray and NMR analysis.Only 5β-ambrox (=1,2,3a,4,5,5aβ,6,7,8,9,9a,9bα-dodecahydro-3aβ,6,6,9aβ-tetramethylnaphthofuran; 5) has an odor quality comparable to Ambrox.The 1,3-synperiplanar/diaxial conformation of the substituents at C(8) (=C(3a)) and C(10) (=C(9a)) has thus been confirmed to be a compulsory structure element for the particular odor.
Triterpenoid Total Synthesis, I: Synthesis of Ambrein and Ambrox
Mori, Kenji,Tamura, Hiroshi
, p. 361 - 368 (2007/10/02)
The first total synthesis of (+)-ambrein (1), a triterpene alcohol isolated from ambergris, was achieved.Both the enantiomers of ambrox (2) were also synthesized.
110. The Synthesis of Racemic Ambrox
Buechi, George,Wueest, Hans
, p. 996 - 1000 (2007/10/02)
(+/-)-Ambrox (10), the racemic form of (-)-Ambrox, the commercially most important ambergris odorant has been synthesized from a readily available bicyclic keto ester in five steps.The racemic ether retains the characteristic scent of fine-quality ambergris, and the odor threshold of the racemate and the (-)-enantiomer prepared from natural sclareol found to be essentially identical.
212. Significance of the Geminal Dimethyl Group in the Odor Principle of Ambrox
Ohloff, Guenther,Giersch, Wolfgang,Pickenhagen, Wilhelm,Furrer, Anton,Frei, Beatrice
, p. 2022 - 2029 (2007/10/02)
The diastereoisomeric 18-nor- and 19-norambrox ((6α)- and (6β)-dodecahydro-3a,6,9a-trimethylnaphtholfurans resp.) as well as the corresponding 18,19-dinor-derivatives (dodecahydro-3a,9a-dimethylnaphthofurans) have been synthesized and subjected to sensory evaluation.Threshold data and odor determination give an enlarged insight into the structure-activity relationship (SAR) in ambrox-type ambergris fragrances.As a general conclusion, the accumulation of axial CH3 groups in the tricyclic ethers 1-12 leads to the strongest receptor affinity.
