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Polyacetylene type cowbane extract (S)-Virol C and synthetic method thereof

A technology of extract and polyyne, which is applied in the field of asymmetric synthesis of hemlock extract-VirolC, can solve the problems of difficult extraction and synthesis methods, decomposition and deterioration, and achieve cost reduction, simplification of reaction operation and synthesis route, and preparation process Efficient and environmentally friendly effect

Inactive Publication Date: 2016-05-18
HENAN AGRICULTURAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Since the extract of toxin is often a polyalkyne compound containing chiral alcoholic hydroxyl groups, it will decompose and deteriorate when exposed to air or exposed to light, and it is difficult to obtain by extraction and synthesis methods

Method used

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  • Polyacetylene type cowbane extract (S)-Virol C and synthetic method thereof
  • Polyacetylene type cowbane extract (S)-Virol C and synthetic method thereof
  • Polyacetylene type cowbane extract (S)-Virol C and synthetic method thereof

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Embodiment Construction

[0022] The following examples further illustrate the content of the present invention, but should not be construed as limiting the present invention.

[0023] 1. Synthesis of (S)-VirolC(I):

[0024] Under nitrogen protection, in a 10mL Shrek tube equipped with a magnetic stirrer, add cuprous iodide (57mg, 0.3mmol), tetrakistriphenylphosphine palladium (86mg, 0.75mmol), (S, E)-1 -Bromo-1-ene-3-decanol (II) (1.5mmol) and 3mL of benzene, stirred evenly, reacted at room temperature for 3 minutes, then added 4,6-diyne-1-heptanol (III) (1.5 mmol) and triethylamine (2 mL, 15 mmol), react overnight at room temperature. The reaction was quenched by adding 3 mL of saturated ammonium chloride solution. The aqueous phase was extracted with ether, the obtained organic phase was dried with anhydrous sodium sulfate, and the crude product was obtained by distillation under reduced pressure. Finally, it was purified by silica gel column chromatography (petroleum ether / ethyl acetate=10 / 1) to...

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Abstract

The invention discloses a polyacetylene type cowbane extract (S)-Virol C having a following chemical formula shown in the specification. The synthesis of the polyacetylene type cowbane extract (S)-Virol C does not need a chiral source reagent; and as an asymmetric addition method is adopted to obtain an important intermediate with high optical activity, the cost is reduced and the reaction operation and a synthetic route are simplified to ensure that the preparation process is more efficient and environment-friendly.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis of natural products, and in particular relates to an asymmetric synthesis method of hemlock extract (S)-VirolC. Background technique [0002] Hemlock (Apiaceae, Hemlock), considered one of the most poisonous plants. Hemlock contains a class of chiral polyalkyne compounds including toxin, which has strong cytotoxicity. In 1999, Ohta discovered (S)-VirolC (Tetrahedron1999, 55, 12087) in the extract of hemlock hemlock, as shown in formula (I). Studies have shown that this type of compound is usually a potent, non-competitive γ -Aminobutyric acid (GABA) receptor antagonists, used in pharmaceutical research (Journal of Medicinal Chemistry 2000, 43, 4508). [0003] [0004] Since the toxin extract is often a polyacetylenic compound containing a chiral alcoholic hydroxyl group, exposure to the air or exposure to light will cause its decomposition and deterioration, and it is difficult to ...

Claims

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Application Information

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IPC IPC(8): C07C33/04C07C29/32
CPCC07C67/31C07C29/00C07C29/17C07C29/32C07C29/62C07C69/732C07C33/042C07C33/426C07C33/423C07C33/04
Inventor 那日松刘佳李洪连郭线茹孟灏光杨新玲王登尹新明蒋士军张猛陈琳琳卢世超侯伯男
Owner HENAN AGRICULTURAL UNIVERSITY
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