Method for synthesizing natural product Jaspine B isomer

A technology for natural products and isomers, applied in the production of bulk chemicals, organic chemistry, etc., which can solve the problems of slow speed, easy racemization of chiral centers, and long synthetic routes.

Inactive Publication Date: 2014-02-26
JIANGXI SCI & TECH NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The route designs and methods of the reported synthetic natural product Jaspine B all adopt the classic conventional reactions in organic synthesis, and the synthetic routes are relatively long, and some reactions have slow rates, low yields, many side reactions, and chiral centers. Prone to problems such as racemization

Method used

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  • Method for synthesizing natural product Jaspine B isomer
  • Method for synthesizing natural product Jaspine B isomer

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Embodiment 1

[0028] 1. Synthesis of Compound of Formula 1

[0029] L - Serine (4.2g, 40mmol) was dissolved in 200mL of methanol, cooled to 0°C, and a solution of thionyl chloride (3.2mL, 44mmol) was added. The solution was heated slowly to reflux, then refluxed overnight. After the reaction was complete, the solution was cooled to room temperature, and the solvent was removed under reduced pressure to obtain a white crystalline solid, i.e. L - Serine methyl ester hydrochloride 1 (6.1 g, 100% yield).

[0030] Synthesis of Formula 2 Compounds

[0031] Will L - Serine methyl ester hydrochloride 1 (6.0g, 38.7mmol) was dissolved in 200mL of dichloromethane, cooled to 0°C, 2mL of triethylamine was added dropwise, and stirred for 5 minutes. Then Boc anhydride (8.7 g, 38.7 mmol) was added dropwise. After stirring for 10 minutes, the ice-water bath was removed and the suspension was stirred overnight at room temperature. After the solvent was removed under reduced pressure, saturated a...

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Abstract

The invention relates to a method for synthesizing natural product Jaspine B isomer, which comprises the following steps: by using cheap and accessible L-serine as an initial raw material, carrying out methyl ester protection, propylidene protection, diisobutylaluminum hydride reduction, Corey-Fuchs reaction, alkylation and the like to complete the synthesis of an intermediate disclosed as Formula 6; carrying out a metal catalysis process (silver nitrate catalysis) to complete the synthesis of a key intermediate disclosed as Formula 8; and completing the complete synthesis of the target molecule disclosed as Formula 10 at higher yield. The method has the advantages of novel and reasonable synthetic route design, cheap and accessible raw material, simple operating technique, mild reaction conditions and single product structure, efficiently completes the complete synthesis of the Jaspine B isomer with three chiral centers, and establishes firm foundation for subsequent complete synthesis of the natural product Jaspine B.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for synthesizing Jaspine B isomers. technical background [0002] Jaspine B (aka Pachatrissamine ,like figure 1 ) is Higa. and staff in 2002 from the sponge Pachastissa sp. and Jaspis sp. A furan-containing sphingosine compound isolated for the first time in Jaspine B is the first molecular case in natural products with the structural characteristics of dehydrosphingosine. From the perspective of structural characteristics, Jaspine B has three consecutive chiral centers on the tetrahydrofuran structure skeleton, and the three chiral centers from C-2 to C-4 are all syn -structure. It is effective against cancer cells such as P388, A 549, HT29 and MEL28 in 10ng / mL It shows a good inhibitory effect at a low level, and its excellent anticancer biological activity and novel structural characteristics have attracted many chemical synthesis and drug research worker...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/22
CPCY02P20/55C07D307/22
Inventor 王晓季黄双平唐琳钧陈世鹏王李平吕常山李玉萍
Owner JIANGXI SCI & TECH NORMAL UNIV
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