An efficient, highly enantioenriched route to L-carnitine and α-lipoic acid via hydrolytic kinetic resolution

被引:18
|
作者
Bose, D. Sublias [1 ]
Fatima, Liyakat [1 ]
Rajender, Salla [1 ]
机构
[1] Indian Inst Chem Technol, Fine Chem Lab, Div Organ Chem 3, Hyderabad 500007, Andhra Pradesh, India
来源
SYNTHESIS-STUTTGART | 2006年 / 11卷 / 11期
关键词
L-carnitine; alpha-lipoic acid; hydrolytic kinetic resolution; terminal epoxide; enantioenriched;
D O I
10.1055/s-2006-942363
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general and practical approach for the synthesis of C-4 chiral building blocks using Jacobsen's hydrolytic kinetic resolution technique to resolve terminal epoxides and diols in high enantiomeric excess and excellent yields is described. The utilization of these building blocks for the synthesis of biologically important natural products L-carnitine and alpha-lipoic acid is illustrated.
引用
收藏
页码:1863 / 1867
页数:5
相关论文
共 50 条
  • [21] The comparisons in protective mechanisms and efficiencies among dietary α-lipoic acid, β-glucan and L-carnitine on Nile tilapia infected by Aeromonas hydrophila
    Lu, Dong-Liang
    Limbu, Samwel Mchele
    Lv, Hong-Bo
    Ma, Qiang
    Chen, Li-Qiao
    Zhang, Mei-Ling
    Du, Zhen-Yu
    FISH & SHELLFISH IMMUNOLOGY, 2019, 86 : 785 - 793
  • [22] The Effect Of L-Carnitine And Alpha Lipoic Acid Administration With Exercise In Old Rats On Energy Metabolism Related To Oxidative Stress Parameters
    Kalkan, Kardelen Kocaman
    Sirin, Neslihan
    Tepe, Atakan
    Gok, Ali
    Altas, Tolga
    Agan, Kagan
    Gulhan, Pinar Yildiz
    Alpay, Merve
    CLINICAL AND EXPERIMENTAL HEALTH SCIENCES, 2024, 14 (02): : 476 - 483
  • [23] L-carnitine and α-lipoic acid improve age-associated decline in mitochondrial respiratory chain activity of rat heart muscle
    Sethumadhavan, Savitha
    Chinnakannu, Panneerselvam
    JOURNALS OF GERONTOLOGY SERIES A-BIOLOGICAL SCIENCES AND MEDICAL SCIENCES, 2006, 61 (07): : 650 - 659
  • [24] Comparative study of antioxidative stress of estradiol, α-lipoic acid and L-carnitine against carbon tetrachloride-induced hepatotoxcity in rats
    Hamzawy, M. A.
    El-Denshary, E. S. M.
    Abdel-Wahhab, M. A.
    Hassan, N. S.
    Bahgat, A. K.
    TOXICOLOGY LETTERS, 2011, 205 : S221 - S222
  • [25] The effect of dietary supplements-based alpha-lipoic acid, acetyl l-carnitine and vitamin B complex in patients with tinnitus
    Gelardi, M.
    Marano, P. G.
    Giancaspro, R.
    Cassano, M.
    JOURNAL OF BIOLOGICAL REGULATORS AND HOMEOSTATIC AGENTS, 2022, 36 (01): : 25 - 33
  • [26] The effectiveness of dietary supplements based on alpha-lipoic acid, acetyl l-carnitine and vitamin B complex in the treatment of craniofacial neuralgia
    Gelardi, M.
    Marano, P. G.
    Giancaspro, R.
    Cassano, M.
    JOURNAL OF BIOLOGICAL REGULATORS AND HOMEOSTATIC AGENTS, 2022, 36 (01): : 15 - 23
  • [27] Synthesis of chiral (α,α-difluoroalkyl)phosphonate analogues of (Lyso)phosphatidic acid via hydrolytic kinetic resolution
    Xu, Y
    Prestwich, GD
    ORGANIC LETTERS, 2002, 4 (23) : 4021 - 4024
  • [28] L-carnitine Improved the Cardiac Function via the Effect on Myocardial Fatty Acid Metabolism in a Hemodialysis Patient
    Kaneko, Mai
    Fukasawa, Hirotaka
    Ishibuchi, Kento
    Niwa, Hiroki
    Yasuda, Hideo
    Furuya, Ryuichi
    INTERNAL MEDICINE, 2018, 57 (24) : 3593 - 3596
  • [29] L-Carnitine and DL-α-lipoic acid reverse the age-related deficit in glutathione redox state in skeletal muscle and heart tissues
    Kumaran, S
    Savitha, S
    Devi, MA
    Panneerselvam, C
    MECHANISMS OF AGEING AND DEVELOPMENT, 2004, 125 (07) : 507 - 512
  • [30] L-Amino Acid Amides via Dynamic Kinetic Resolution
    Tessaro, Davide
    Cerioli, Lorenzo
    Servi, Stefano
    Viani, Fiorenza
    D'Arrigo, Paola
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (13) : 2333 - 2338