Method for synthesizing cyclopamine from veratramine

By simplifying the cyclopamine synthesis route and using reseramine to perform Birch reduction and hydrogenation reactions, the complex problems in the existing technology are solved, and efficient and concise cyclopamine synthesis is achieved, which is suitable for large-scale preparation.

CN119708111APending Publication Date: 2025-03-28EAST CHINA NORMAL UNIV
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Patent Information

Application Number
CN202311272480.2
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2023-09-28
Publication Date
2025-03-28

AI Technical Summary

Technical Problem

In the prior art, the synthesis steps of cyclopamine are complex and difficult to achieve efficient and large-scale preparation.

Method used

Resveratramine is used as the initial raw material, and the synthesis route is simplified and the step efficiency is improved through Birch reduction, hydrogenation reaction, amine protection reaction, epoxidation reaction, acid-catalyzed epoxy ring opening, elimination reaction and protective group removal reaction.

Benefits of technology

The efficient synthesis of cyclopamine is achieved, the steps are simplified, the production efficiency is improved, and the large amount of cyclopamine with high drug activity can be prepared.

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Abstract

The invention discloses a method for synthesizing cyclopamine from veratramine. According to the method, veratramine is used as an initial raw material, and Birch reduction, hydrogenation reaction, amino protection reaction, epoxidation reaction, acid-catalyzed epoxy ring opening, elimination reaction and protecting group removal reaction are performed to obtain the veratramine isosteroid alkaloid cyclopamine with high pharmaceutical activity. The method is reasonable in synthetic route design, simple and efficient in step, easy for large-scale preparation of target natural products and wide in application prospect.
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