Synthesis of (R)- and (S)- muscone
| Autor: | Keisuke Yoshikawa, Masamichi Itoh, Satoko Fujimoto, Takeshi Kitahara |
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| Rok vydání: | 2002 |
| Předmět: |
Ketone
Spectrophotometry Infrared Stereochemistry Metathesis Applied Microbiology and Biotechnology Biochemistry Chemical synthesis Analytical Chemistry chemistry.chemical_compound Moschus moschiferus Molecular Biology chemistry.chemical_classification Olefin fiber biology Molecular Structure Organic Chemistry Enantioselective synthesis Cycloparaffins General Medicine biology.organism_classification Muscone Perfume chemistry Odorants Enantiomer Biotechnology |
| Zdroj: | Bioscience, biotechnology, and biochemistry. 66(6) |
| ISSN: | 0916-8451 |
| Popis: | (R)-(-)-Muscone (3-methylcyclopentadecanone, 1) the key perfumery component isolated from the male musk deer, Moschus moschiferus,* was synthesized from the easily available chiral building block, (R)-3-tert-butoxycarbonyl-2-methylpropanoic acid (2), by employing ring-closing olefin metathesis (RCM). Antipode (+)-1 was also synthesized in a similar manner from tert-butyl (S)-3-methoxycarbonylbutanoate (10). *(a) Walbaum, H. J. J. Prakt. Chem., 73, 488 (1906); (b) Ruzicka, L., Further considerations on the constitution of muscone. Helv. Chim. Acta, 9, 715, 1008-1017 (1926). |
| Databáze: | OpenAIRE |
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