A new method for the total synthesis of 13a-hydroxysiliphenine

A technology of total synthesis of hydroxysilicate, applied in organic chemistry, bulk chemical production, etc., can solve the problems of blank synthesis of 13a-hydroxysilicate, less separation content, no synthesis research, etc., and achieve novel structure , mild reaction conditions and high yield

Active Publication Date: 2019-07-26
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, its isolated content is relatively small, and since the first report, there has not been any synthesis research and biological activity report
[0005] Although the synthetic route of common phenanthrene and indolizidine alkaloids has been developed more, the synthesis of 13a-hydroxysilicate is still blank

Method used

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  • A new method for the total synthesis of 13a-hydroxysiliphenine
  • A new method for the total synthesis of 13a-hydroxysiliphenine
  • A new method for the total synthesis of 13a-hydroxysiliphenine

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Embodiment Construction

[0021] Synthesis of Intermediate 1: Add sodium iodide (27.9g, 0.186mol), 15mL tetrahydrofuran, and 30mL acetonitrile into a 500mL single-necked bottle, add benzoyl chloride (17.3ml, 0.15mol) dropwise in an ice bath, and complete the addition in about half an hour , react overnight at room temperature. The reaction solvent was distilled off under reduced pressure, the residue was diluted with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and precipitated to obtain 43.2 g of a colorless liquid with a yield of 95%. 1 H NMR (400MHz, CDCl 3 ): δ8.01(m, 2H), 7.53(t, J=7.3Hz, 1H), 7.43(t, J=7.8Hz, 2H), 4.34(t, J=6.4Hz, 2H), 3.24(t , J=6.8Hz, 2H), 1.88-1.99(m, 4H).

[0022] Synthesis of Intermediate 2: Add 1 (21.6g, 0.071mol), 100mL DMF, and sodium azide (6.92g, 0.107mol) to a 500mL single-necked bottle, and react at room temperature for 6h. The reaction solution was diluted with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, a...

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Abstract

The invention relates to a total synthesis route and method of 13a-hydroxy tylophorine. The method comprises the following steps: synthesizing siloxane nitrile alcohol containing nitrogen from tetrahydrofuran and benzoyl chloride which are simple and easily available, and coupling siloxane nitrile alcohol with a philippine benzyl bromide compound by virtue of a polarity-reversal concept; constructing important lactone by virtue of butyl lithium accelerated acyl rearrangement / acid catalysis esterification; and carrying out tandem reduction so as to obtain novel-structure phenanthro-aza nine-membered ring structure, and carrying out subsequent functionalization, so as to obtain required 13a-hydroxy tylophorine. According to the method, the total synthesis of 13a-hydroxy tylophorine is realized for the first time, the raw materials are easily available, the operation is simple and convenient, the yield is relatively high, and the raw material is provided for the biological activity research. The specific synthesis steps are detailed in description.

Description

technical field [0001] The invention relates to a total synthesis route of 13a-hydroxysilicateline, which belongs to the technical field of organic chemistry. Background technique [0002] Phenanthrene and indolizidine alkaloids are a class of alkaloids containing a phenanthrene [6,5] nitrogen heterocycle in their structure, and mainly exist in plants of the following four families: Romoaceae, Moraceae, Acanthaceae and Lauraceae. So far, more than 60 members of this family have been isolated and characterized, all of which have the same five-ring structure, and the main difference lies in the position and quantity of methoxy or hydroxyl substitution on the phenanthrene ring. Since the first phenanthrene and indolizidine alkaloid, sillimenine, was isolated in 1935, the unique biological activity of this alkaloid has also received extensive attention. Phenanthrene and indolizidine alkaloids have broad-spectrum biological activities and exhibit good anti-cancer, anti-leukemia...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCY02P20/55
Inventor 汪清民张辉刘玉秀王兹稳
Owner NANKAI UNIV
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