Stereochemistry of terpene derivatives. Part 8: synthesis of novel terpenoids from (1S,4R)- and (1R,4S)-fenchone and their comparative odour characteristics

被引:9
|
作者
Strub, Daniel Jan [1 ]
Balcerzak, Lucyna [1 ]
Niewiadomska, Maria [1 ]
Kula, Jozef [2 ]
Sikora, Magdalena [2 ]
Gibka, Julia [2 ]
Lochynski, Stanislaw [1 ,3 ]
机构
[1] Wroclaw Univ Technol, Fac Chem, Dept Bioorgan Chem, PL-50370 Wroclaw, Poland
[2] Tech Univ Lodz, Fac Biotechnol & Food Sci, Inst Gen Food Chem, PL-90924 Lodz, Poland
[3] Wroclaw Coll Physiotherapy, Inst Cosmetol, PL-50038 Wroclaw, Poland
关键词
FRAGRANCE COMPOUNDS; OXIME ETHERS; SERIES; SYSTEM; OIL;
D O I
10.1016/j.tetasy.2014.06.012
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
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.
引用
收藏
页码:1038 / 1045
页数:8
相关论文
共 50 条
  • [1] INVESTIGATION OF A CHIRAL MASKED KETENE SYNTHON SYNTHESIS OF THE (+)-(1R,4R) AND (-)-(1S,4S) ENANTIOMERS OF DEHYDRONORCAMPHOR
    MAIGNAN, C
    RAPHAEL, RA
    TETRAHEDRON, 1983, 39 (20) : 3245 - 3249
  • [2] Development of a Stereoselective Synthesis of (1R,4R)- and (1S,4S)-2-Oxa-5-azabicyclo[2.2.2]octane
    Maddess, Matthew L.
    Cleator, Ed
    Morimoto, Mariko
    Goodyear, Adrian
    Dieguez-Vazquez, Alejandro
    Gibb, Andrew
    Kirtley, Andy
    Wang, Jie
    Qi, Ji
    Kong, Lingzhu
    Alam, Mahbub
    Keen, Stephen
    Oliver, Steven F.
    Wen, Xin
    Lam, Yu-Hong
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2022, 26 (03) : 640 - 647
  • [3] Biotransformation of (-)-(1R,4S)-Menthone and (+)-(1S,4R)-Menthone by the Common Cutworm Spodoptera litura Larvae
    Marumoto, Shinsuke
    Okuno, Yoshiharu
    Hagiwara, Yuki
    Miyazawa, Mitsuo
    JOURNAL OF OLEO SCIENCE, 2017, 66 (08) : 883 - 888
  • [4] Synthesis of (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus, its racemate, (1R,4R)- and (1S,4S)-isomers
    Mori, Kenji
    TETRAHEDRON-ASYMMETRY, 2006, 17 (14) : 2133 - 2142
  • [5] Stereocontrolled Synthesis of (1R,3R,4S)- and (1S,3R,4S)-3,4-diaminocyclopentanols
    Guan, YS
    Green, MA
    Bergstrom, DE
    SYNLETT, 1999, (04) : 426 - 428
  • [6] First Stereoselective Synthesis of (1R,2R,4R)- and (1S,2R,4S)-2-Substituted-1-azabicyclo[2.2.1]heptanes
    Etayo, Pablo
    Badorrey, Ramon
    Diaz-de-Villegas, Maria D.
    Galvez, Jose A.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (09) : 1372 - 1376
  • [7] Synthesis of antibiofilm (1R,4S)-(-)-fenchone derivatives to control Pseudomonas syringae pv. tomato
    Wang, Delong
    Li, Yunpeng
    Li, Linjing
    Chen, Yizhe
    Min, Shuoling
    Wang, Yong
    Feng, Juntao
    Zhou, Jianbo
    Zhang, Zhijia
    Fang, Yali
    PEST MANAGEMENT SCIENCE, 2025, 81 (03) : 1261 - 1273
  • [8] Asymmetric syntheses of (1r,3R,4S)- and (1s,3R,4S)-(3,4-difluorocyclopentyl)-alanine derivatives
    Simpson, Robert D.
    Zhao, Wei
    TETRAHEDRON-ASYMMETRY, 2009, 20 (13) : 1515 - 1520
  • [9] STEREOCHEMISTRY .39. STEREOCHEMISTRY OF (1R,4S) MENTHONE ACYLATION
    POTAPOV, VM
    GRISHINA, GV
    TALEBAROVSKAYA, IK
    ZHURNAL ORGANICHESKOI KHIMII, 1976, 12 (07): : 1410 - 1415
  • [10] Biotransformation of (+)-(1R,2S,4R)-borneol and (-)-(1S,2R,4S)-borneol by Spodoptera litura (common cutworm) larvae
    Marumoto, Shinsuke
    Okuno, Yoshiharu
    Miyamoto, Yohei
    Miyazawa, Mitsuo
    JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2015, 115 : 160 - 167