- Formal synthesis of (±)-Ambrox
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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.
- Barco, Achille,Benetti, Simonetta,Bianchi, Anna,Casolari, Alberto,Guarneri, Mario,Pollini, Gian P.
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p. 8333 - 8338
(2007/10/02)
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- Ambergris compounds from labdanolic acid
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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.
- Urones,Basabe,Marcos,Gonzalez,Jimenez,Sexmero,Lithgow
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p. 9991 - 9998
(2007/10/02)
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- A formal synthesis of (±)-Ambrox
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Bicyclic diol 6, a direct precursor of (±)-Ambrox ((±)-7), has been synthesised in four steps (35% yield) from the known bicyclic enone 2.
- Snowden,Linder
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p. 4119 - 4120
(2007/10/02)
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- Configuration-Odor Relationship in 5β-Ambrox
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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.
- Escher, Sina,Giersch, Wolfgang,Niclass, Yvan,Bernardinelli, Gerald,Ohloff, Guenther
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p. 1935 - 1947
(2007/10/02)
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- Triterpenoid Total Synthesis, I: Synthesis of Ambrein and Ambrox
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The first total synthesis of (+)-ambrein (1), a triterpene alcohol isolated from ambergris, was achieved.Both the enantiomers of ambrox (2) were also synthesized.
- Mori, Kenji,Tamura, Hiroshi
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p. 361 - 368
(2007/10/02)
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- 110. The Synthesis of Racemic Ambrox
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(+/-)-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.
- Buechi, George,Wueest, Hans
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p. 996 - 1000
(2007/10/02)
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