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The Total Synthesis of Scutellarin-7-O-glucuronide

Author: ChenZuoZhi
Tutor: YangJian
School: Kunming University of Science and Technology
Course: Medicinal Chemistry
Keywords: Scutellarin-7-O-glucuronide 3,4,5-Trimethoxyphenol chalcone route synthesis
CLC: R284.1
Type: Master's thesis
Year: 2009
Downloads: 51
Quote: 0
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Abstract


Scutellarin-7-O-glucuronide, which is firstly extracted from Erigeron breviscapus, is a definitely pharmacologically active natural product. It is wildely used in clinical application to threat stroke and it’s commemorative, the coronary heart disease, hyperviscosity syndrome, squamous carcinX and so on. In this thesis work, we prepared the title compound from 3,4,5-trimethoxybenzoicacid or 3,4,5-trimethoxybenzaldehyde. We synthesized 3,4,5-trimethoxyphenol by two ways, and a improved mothed to synthesize the 5,6,7,4’-Tetramethoxyflavone was carried out. After that, we made a one-step reaction to demethylated and acetylized it to get 5,6,7,4’-tetraacetatescutellarein. Then, benzyl substitution was made to synthesize 7-(benzyloxy)-5,6,4’-triacetateflavone and following hydrogenated in the presence of palladium to remove the benzyloxy. On the other hand, we prepared the 2,3,4-tri-O-acetyl-l-bromo-l-deoxy-β-D-galacturonate starting from D-glucuronolactone by trans-esterification and acetylation. Let it connect with the 7-hydroxyl-5,6,4’-triacetateflavone and then deacetylated to get the target compound. This route features with the preparation of the 3,4,5-Trimethoxypheno by two mothed, and a novel synthesis of 5,6,7,4-Tetramethoxyflavone. The overall yield is 22%.Furthermore, in our study work, we made use of single variable analysis to optimize the conditions of several reaction steps.In a word, we succeed to synthesize the high-purity and pharmaceutically acceptable scutellarin-7-O-glucuronide. The whole intermediates and the target compound were confirmed by 1HNMR or MS. In addition, we took the yield to a ideal level by research for the condition of reaction.

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