Stereoselective Synthesis of the Antileukemic Sesquiterpene (+)-Caparratriene from L-menthol and Tiglic Aldehyde

被引:5
|
作者
Vydrina, V. A. [1 ]
Kravchenko, A. A. [1 ]
Yakovleva, M. P. [1 ]
Ishmuratova, N. M. [1 ]
Ishmuratov, G. Yu. [1 ]
机构
[1] Russian Acad Sci, Ufa Inst Chem, 71 Prosp Oktyabrya, Ufa 450054, Russia
关键词
(+)-caparratriene; L-menthol; tiglic aldehyde; Wittig reaction; (R)-(-)-citronellylbromide;
D O I
10.1007/s10600-018-2379-y
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A stereoselective synthesis of natural (+)-caparratriene was developed starting from commercially available L-menthol and tiglic aldehyde. The key step was a Wittig reaction of the latter with the triphenylphosphorane generated from (R)-(-)-citronellyl bromide. (+)-Caparratriene as a mixture (4:1) of 2E,4E- and 2E,4Z-stereoisomers is a known anticancer agent.
引用
收藏
页码:461 / 463
页数:3
相关论文
共 50 条
  • [31] Synthesis of L-menthol lactate using acidic ionic liquid [Hnmp]+ HSO4- as catalyst
    张爱华
    肖志红
    刘汝宽
    张良波
    李培旺
    李力
    湖南林业科技, 2011, (04) : 8 - 11
  • [32] PRODUCTION OF L-MENTHOL AND L-MENTHYL ESTERS FROM RACEMIC SUBSTRATES BY ESTER HYDROLYSIS AND ESTER SYNTHESIS USING CANDIDA-CYLINDRACEA LIPASE
    SYLDATK, C
    LOKOTSCH, W
    FRITSCHE, K
    DECHEMA BIOTECHNOLOGY CONFERENCES, VOL 3, PTS A AND B, 1989, 3 : 141 - 144
  • [33] The Influence of the Solid Solution Formation on Purification of L-Menthol from the Enantiomer Mixture by Three-Phase Crystallization
    Hsu, Yu-Chao
    Yang, Sheng-Chin
    Ku, Kai-Fang
    Shiau, Lie-Ding
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2023, 24 (19)
  • [34] Stereoselective Formal Total Synthesis of (-)-Swainsonine from Garner's Aldehyde
    Murthy, Sabbavarapu Narayana
    Nageswar, Yadavalli Venkata Durga
    SYNTHESIS-STUTTGART, 2011, (05): : 755 - 758
  • [35] Highly selective aluminium-catalysed intramolecular Prins reaction for L-menthol synthesis (vol 4, pg 61619, 2014)
    Itoh, H.
    Maeda, H.
    Yamada, S.
    Hori, Y.
    Mino, T.
    Sakamoto, Masami
    RSC ADVANCES, 2015, 5 (79): : 64300 - 64302
  • [36] Synthesis of the juvenoid (S)-(+)-hydroprene from L-(-)-menthol
    Kharisov, RY
    Gazetdinov, RR
    Ishmuratov, GY
    Tolstikov, GA
    CHEMISTRY OF NATURAL COMPOUNDS, 2001, 37 (02) : 140 - 142
  • [37] In-vitro and In-silico study on the acylation reaction of (-)-Isopulegol and L-Menthol Mixtures with Lipase from Rhizomuchor miehei
    Iftitah, Elvina Dhiatul
    Yulasandini, Izma Fitria
    Utomo, Edi Priyo
    9TH ANNUAL BASIC SCIENCE INTERNATIONAL CONFERENCE 2019 (BASIC 2019), 2019, 546
  • [38] Enhancing the Enantioselectivity and Catalytic Efficiency of Esterase from Bacillus subtilis for Kinetic Resolution of L-Menthol through Semirational Design
    Zhou, Jiawei
    Sang, Yumin
    Wang, Zhuang
    Feng, Jiacheng
    Zhu, Linjiang
    Chen, Xiaolong
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2024, 72 (04) : 2277 - 2286
  • [39] Synthesis of the Juvenoid (S)-(+)-Hydroprene from L-(-)-Menthol
    R. Ya. Kharisov
    R. R. Gazetdinov
    G. Yu. Ishmuratov
    G. A. Tolstikov
    Chemistry of Natural Compounds, 2001, 37 : 140 - 142
  • [40] Efficient production of l-menthyl α-glucopyranoside from l-menthol via whole-cell biotransformation using recombinant Escherichia coli
    Luyi Chen
    Yuanlu Zhou
    Changxin Lu
    Zhi Ma
    Hanchi Chen
    Linjiang Zhu
    Yuele Lu
    Xiaolong Chen
    Biotechnology Letters, 2021, 43 : 1757 - 1764