A Practical and Economical High-Yielding, Six-Step Sequence Synthesis of a Flavone: Application to the Multigram-Scale Synthesis of Ladanein

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• 作者：Xavier Martin-Benlloch ; Mourad Elhabiri ; Don Antoine Lanfranchi ; Elisabeth Davioud-Charvet
• 刊名：Organic Process Research & Development
• 出版年：2014
• 出版时间：May 16, 2014
• 年：2014
• 卷：18
• 期：5
• 页码：613-617
• 全文大小：267K
• 年卷期：v.18,no.5(May 16, 2014)
• ISSN：1520-586X

文摘

Herein we report a short and economic synthesis of the antiviral flavonoid lead ladanein (1). Ladanein is obtained from 2,6-dimethoxyquinone (11) in six steps with 51% overall yield. After a high-yielding reductive acetylation and Fries rearrangement, the flavone skeleton is built by means of a Baker鈥揤enkataraman rearrangement. Throughout the synthetic pathway no chromatographic columns were used, and the reaction products were isolated and purified by optimized work-up and crystallization processes. This new process has been tested on a multigram-scale with an improved overall yield from 16 to 51% through six steps, and three chromatographic purifications used in the earlier synthesis were eliminated.