Enantioselective synthesis of (-)-beta-santalol by a copper-catalyzed enynol cyclization-fragmentation reaction
| Autor: | Charles Fehr, Iris Magpantay, Xavier Marquet, Jeremy Arpagaus, Magali Vuagnoux |
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| Rok vydání: | 2009 |
| Předmět: |
Sandalwood oil
Sandalwood biology Chemistry Cyclopropanation Enantioselective synthesis General Medicine General Chemistry β-Santalol biology.organism_classification Catalysis Cyclopropane chemistry.chemical_compound Cycloisomerization Fragmentation (mass spectrometry) medicine Organic chemistry medicine.drug |
| Zdroj: | Angewandte Chemie (International ed. in English). 48(39) |
| ISSN: | 1521-3773 |
| Popis: | We report herein the first enantioselective, direct synthesis of the highly prized natural sandalwood odorant ( )-b-santalol (( )-1). The key step in the synthesis is an efficient copper-catalyzed rearrangement of an enynol. The increasing scarcity of East Indian sandalwood oil has motivated research chemists over the last 40 years to develop a synthesis of the most valuable component, ( )-b-santalol ( )-1, which makes up 20–25% of the composition of the oil, or its racemate. Despite extensive efforts, this excellent fragrance ingredient is still not commercially available. Recently, we reported the cost-efficient copper-catalyzed cycloisomerization of 5-en-1-yn-3-ols (cyclopropanation/1,2alkyl shift; Scheme 1, A!E) and related enynol esters. |
| Databáze: | OpenAIRE |
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