Stereochemistry of terpene derivatives. Part 8: synthesis of novel terpenoids from (1S,4R)- and (1R,4S)-fenchone and their comparative odour characteristics
O-alkylation of (+) and (-)-fenchone oximes with various alkyl halides led to 20 novel ethers. Better results were obtained when mild reaction conditions were employed (i.e., aprotic, polar solvent and room temperature). The hydrolytic kinetic resolution of the O-glycidyl derivative was carried out using cobalt-salen catalysts. The best results were obtained when using (-)-(R,R)-catalyst: (-)-(R)-isomer was obtained with >90% de. The use of a (+)-(S,S)-catalyst gave the (-)-(S)-epoxide with only 67% de. However, the (S)-epoxide was obtained with >90% de when the (-)-(R)-diol was subjected to the Mitsunobu reaction. Significant fragrance diversity was observed between the homologous series of fenchone oxime ethers. More agreeable are scents of ethers derived from (-)-fenchone oxime. Their odours range from turpentine like and resinous to vegetable, floral or woody whereas the scents of (+)-ethers range from turpentine, resinous to onion like and slightly floral. (C) 2014 Elsevier Ltd. All rights reserved.
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Kindai Univ, Joint Res Ctr, Higashiosaka, Osaka 5778502, JapanKindai Univ, Joint Res Ctr, Higashiosaka, Osaka 5778502, Japan
Marumoto, Shinsuke
Okuno, Yoshiharu
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Wakayama Natl Coll Technol, Dept Mat Sci, Gobo, Wakayama 6440023, JapanKindai Univ, Joint Res Ctr, Higashiosaka, Osaka 5778502, Japan
Okuno, Yoshiharu
Hagiwara, Yuki
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Kindai Univ, Dept Appl Chem, Higashiosaka, Osaka 5778502, JapanKindai Univ, Joint Res Ctr, Higashiosaka, Osaka 5778502, Japan
Hagiwara, Yuki
Miyazawa, Mitsuo
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Nara Inst Sci & Technol, Grad Sch Mat Sci, Nara 6300192, Japan
Osaka City Univ, Grad Sch Sci, Osaka 5588583, Japan
Kindai Univ, Dept Appl Chem, Higashiosaka, Osaka 5778502, JapanKindai Univ, Joint Res Ctr, Higashiosaka, Osaka 5778502, Japan