Stereochemistry of terpene derivatives. Part 6: Chemoenzymatic synthesis of chiral bicyclo[3.1.0]hexane derivatives with olfactory properties

被引：7
作者：
Kuriata, Renata [1 ]
Gajcy, Kamila [1 ]
Turowska-Tyrk, Ilona [2 ]
Lochynski, Stanislaw [1 ,3 ]
机构：
[1] Wroclaw Univ Technol, Dept Bioorgan Chem, Fac Chem, PL-50370 Wroclaw, Poland
[2] Wroclaw Univ Technol, Inst Phys & Theoret Chem, Fac Chem, PL-50370 Wroclaw, Poland
[3] Wroclaw Coll Physiotherapy, Dept Cosmetol, PL-50038 Wroclaw, Poland
来源：
TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 07期
关键词：
BIOCATALYSTS;
D O I：
10.1016/j.tetasy.2010.04.052
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Starting from (+)-3-carene 1, several chiral fragrant compounds with the bicyclo[3 1.0]hexane system were synthesized. These compounds were used as substrates for the biotransformation with lipases as biocatalysts Pure diastereoisomers were obtained and their absolute configuration was confirmed by X-ray crystallography The olfactory properties of new compounds were determined (C) 2010 Elsevier Ltd All rights reserved
引用
收藏
页码：805 / 809
页数：5
相关论文
共 22 条
  • [1] Lipase-catalysed preparation of enantiomerically enriched odorants
    Abate, A
    Brenna, E
    Fuganti, C
    Gatti, FG
    Serra, S
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2004, 32 (1-2) : 33 - 51
  • [2] THE CHIRAL POOL AS A SOURCE OF ENANTIOSELECTIVE CATALYSTS AND AUXILIARIES
    BLASER, HU
    [J]. CHEMICAL REVIEWS, 1992, 92 (05) : 935 - 952
  • [3] Bornscheuer UT, 2006, HYDROLASES IN ORGANIC SYNTHESIS: REGIO- AND STEREOSELECTIVE BIOTRANSFORMATIONS, 2ND EDITION, P1
  • [4] Enantioselective perception of chiral odorants
    Brenna, E
    Fuganti, C
    Serra, S
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (01) : 1 - 42
  • [5] Stereochemistry of terpene derivatives.: Part 5:: Synthesis of chiral lactones fused to a carane system -: insect feeding deterrents
    Fraçkowiak, B
    Ochalik, K
    Bialonska, A
    Ciunik, Z
    Wawrzenczyk, C
    Lochynski, S
    [J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (01) : 124 - 129
  • [6] Stereochemistry of terpene derivatives.: Part 4:: Fragrant terpenoid derivatives with an unsaturated gem-dimethylbicyclo[3.1.0]hexane system
    Frackowiak, B
    Olejniczak, T
    Latajka, R
    Bialonska, A
    Ciunik, Z
    Lochynski, S
    [J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (20) : 3352 - 3360
  • [7] Synthesis and transformation of novel cyclic β-amino acid derivatives from (+)-3-carene
    Gyónfalvi, S
    Szakonyi, Z
    Fülöp, F
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (24) : 3965 - 3972
  • [8] Application of bacteria and fungi as biocatalysts for the preparation of optically active hydroxyphosphonates
    Kafarski, P
    Lejczak, B
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2004, 29 (1-6) : 99 - 104
  • [9] ENZYMES IN ORGANIC-CHEMISTRY, .1. ENANTIOSELECTIVE HYDROLYSIS OF ALPHA-(ACYLOXY)PHOSPHONATES BY ESTEROLYTIC ENZYMES
    LI, YF
    HAMMERSCHMIDT, F
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (01) : 109 - 120
  • [10] Lochynski S, 1997, J SOC COSMET CHEM, V48, P107
123