Synthesis of polyether macrodiolides based on acetylenic derivatives of (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid

被引：0

作者：

I. I. Islamov

A. V. Yusupova

V. A. D’yakonov

U. M. Dzhemilev

机构：

[1] Russian Academy of Sciences,Institute of Petrochemistry and Catalysis, Ufa Federal Research Center

[2] N. D. Zelinsky Institute of Organic Chemistry of Russian Academy of Sciences,undefined

来源：

Russian Chemical Bulletin | 2023年 / 72卷

关键词：

-cyclomagnesiation; 1,2-dienes; -1,5-dienes; polyether macrodiolides; 1,3-diynes;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

The stereoselective synthesis of (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid was carried out using Ti-catalyzed homo-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran. Intermolecular esterification of this dicarboxylic acid with polyether acetylenic alcohols in the presence of carbodiimides was used to synthesize the corresponding monoesters and symmetric diesters. Using the intramolecular oxidative coupling of terminal triple bonds of the latter compounds, polyether macrodiolides containing 1Z,5Z-diene and 1,3-diyne fragments were synthesized.

引用

页码：2473 / 2483

页数：10

共 27 条

[1] Synthesis of polyether macrodiolides based on acetylenic derivatives of (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid
Islamov, I. I.
Yusupova, A. V.
D'yakonov, V. A.
Dzhemilev, U. M.
RUSSIAN CHEMICAL BULLETIN, 2023, 72 (10) : 2473 - 2483
[2] Synthesis of macrocyclic and linear compounds with 1Z,5Z-diene and alkynylcarbinol fragments based on (5Z,9Z)-tetradeca-5,9-diene-1,14-diol
Islamov, I. I.
Makarov, A. A.
Makarova, E. Kh.
Yusupova, A. V.
D'yakonov, V. A.
Dzhemilev, U. M.
RUSSIAN CHEMICAL BULLETIN, 2023, 72 (04) : 925 - 931
[3] Synthesis of macrocyclic and linear compounds with 1Z,5Z-diene and alkynylcarbinol fragments based on (5Z,9Z)-tetradeca-5,9-diene-1,14-diol
I. I. Islamov
A. A. Makarov
E. Kh. Makarova
A. V. Yusupova
V. A. D’yakonov
U. M. Dzhemilev
Russian Chemical Bulletin, 2023, 72 : 925 - 931
[4] Facile syntheses for (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z, 9Z)-5,9-eicosadienoic acid through a common synthetic route
Carballeira, NM
Emiliano, A
Guzmán, A
CHEMISTRY AND PHYSICS OF LIPIDS, 1999, 100 (1-2) : 33 - 40
[5] Catalytic cyclometallation in steroid chemistry V: Synthesis of hybrid molecules based on steroid oximes and (5Z,9Z)-tetradeca-5,9-dienedioic acid as potential anticancer agents
D'yakonov, Vladimir A.
Tuktarova, Regina A.
Dzhemileva, Lilya U.
Ishmukhametova, Svetlana R.
Yunusbaeva, Milyausha M.
Dzhemilev, Usein M.
STEROIDS, 2018, 138 : 14 - 20
[6] Novel Hybrid Molecules on the Basis of Steroids and (5Z,9Z)-Tetradeca-5,9-dienoic Acid: Synthesis, Anti-Cancer Studies and Human Topoisomerase I Inhibitory Activity
D'yakonov, Vladimir A.
Dzhemileva, Lilya U.
Tuktarova, Regina A.
Ishmukhametova, Svetlana R.
Yunusbaeva, Milyausha M.
Ramazanov, Ilfir R.
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ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2017, 17 (08) : 1126 - 1135
[7] (5Z,9Z)-14-[(3,28-Dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic Acid with Cytotoxic Activity
Tuktarova, Regina A.
Dzhemileva, Lilya U.
Dzhemilev, Usein M.
MOLBANK, 2024, 2024 (01)
[8] Synthesis of Amides Based on Biologically Active (5Z,9Z)-Eicosa-5,9-dienoic Acid
Makarova, E. Kh.
Makarov, A. A.
Dzhemilev, U. M.
D'yakonov, V. A.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 60 (03) : 437 - 441
[9] Total synthesis of the antimicrobial fatty acid (5Z,9Z)-14-methylpentadeca-5,9-dienoic acid and its longer-chain analog (5Z,9Z)-24-methylpentacosa-5,9-dienoic acid
Reyes, ED
Carballeira, NM
SYNTHESIS-STUTTGART, 1997, (10): : 1195 - &
[10] Synthesis and Anticancer Activity of Hybrid Molecules Based on Lithocholic and (5Z,9Z)-Tetradeca-5,9-dienedioic Acids Linked via Mono(di,tri,tetra)ethylene Glycol and α,ω-Diaminoalkane Units
D'yakonov, Vladimir A.
Tuktarova, Regina A.
Dzhemileva, Lilya U.
Ishmukhametova, Svetlana R.
Dzhemilev, Usein M.
PHARMACEUTICALS, 2021, 14 (02) : 1 - 29

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