Synthetic method of Reziya base tetracyclic skeleton

A technology of Reziya base and synthesis method, which is applied in the field of synthesizing Reziya base tetracyclic skeleton, can solve problems such as large tension and complex structure, and achieve the effects of efficient route, simple operation steps and economical steps.

Active Publication Date: 2019-09-10
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Complex structure, high tension

Method used

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  • Synthetic method of Reziya base tetracyclic skeleton
  • Synthetic method of Reziya base tetracyclic skeleton
  • Synthetic method of Reziya base tetracyclic skeleton

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Experimental program
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Embodiment Construction

[0036] The present invention will be described in detail below.

[0037] 1) Compound 1 (1.9g, 5.32mmol, 1.0equiv.), silver oxide (3.8g, 16mmol, 3.0equiv.) and tetrabutylammonium iodide (393mg, 1.06mmol, 0.2equiv.) were dissolved in heavy distilled dichloromethane. Then iodomethane (1.66ml, 26.6mmol, 5.0equiv.) was added and reacted overnight at room temperature. Excess methyl iodide was quenched with saturated sodium sulfite, water was added, extracted three times with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The crude product was separated by column to obtain compound 2 (1.67g, 84%, Rf=0.39 (15% ethyl acetate / petroleum ether).

[0038] 1 H NMR (400MHz, CDCl 3 )δ7.41–7.29(m,6H),7.06(dd,J=14.4,3.7Hz,1H),5.53–5.36(m,1H),5.26–5.06(m,2H),4.53(d,J= 46.8Hz, 1H), 4.24–4.08(m, 1H), 3.89(d, J=22.3Hz, 1H), 3.74(s, 3H), 3.61–3.44(m, 4H), 3.31(s, 2H), 1.89(dd,J=27.6,12.6Hz,1H),1.77(dd,J=6.8,2.1Hz,3H).

[0039] 13 C NMR (101MHz, CDCl 3 )...

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Abstract

The invention discloses synthesis methods of a rhazimine tetracyclic skeleton. One of the synthesis methods adopts the following linear synthesis route: gamma-hydroxy-alpha,beta-unsaturated ester having a [3,3,1] ring system structure is adopted an initial raw material; a methanol group protects the hydroxyl group of allyl alcohol, and deconjugation alkylation is creatively used to achieve the migration of a double bond and construct a whole carbon quaternary carbon center; lithium tetrafluoroborate undergoes silicon deprotection and alkenyl ether structure hydrolysis; an aldehydic carbonyl group obtained by oxidizing a primary alcohol and o-iodoaniline undergo reducing amination, and a ketocarbonyl group is reduced; a secondary alcohol is oxidized; and the rhazimine tetracyclic skeleton is constructed through the alpha-position coupling of the carbonyl group. The other one of the synthesis methods adopts the following convergent synthesis route: a methyl-protected allyl alcohol structure and chloride connected with the o-iodoanide fragment undergoes deconjugation alkylation, and then intramolecular coupling is carried out to construct the rhazimine tetracyclic skeleton. The synthesis methods have the advantages of simple operating steps, low requirements of reaction conditions, and high-efficiency synthesis of the target compound.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing the tetracyclic skeleton of raizia base. Background technique [0002] Plants rich in akuammiline alkaloids or their extracts are widely used as folk medicines in many countries and regions. It is precisely because of the medicinal value of these plants or their extracts that aroused the research interests of natural product isolates and pharmacologists. Since the content of akumilin alkaloids is the largest, the akumilin alkaloids are collectively referred to as the natural products of this family. Scientific research has found that acumilin alkaloids have good biological activities such as anti-cancer, bactericidal, anti-inflammatory, cough-relieving, and anti-malarial. Through subsequent medicinal chemistry research, acumilin alkaloids may show their charm in pharmaceutical applications. [0003] Structurally, this class of al...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/08
Inventor 纪跃王丹高栓虎
Owner EAST CHINA NORMAL UNIV
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