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Open AccessArticle

Total Synthesis of Six 3,4-Unsubstituted Coumarins

1
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, China
2
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, China
*
Author to whom correspondence should be addressed.
Molecules 2013, 18(12), 15613-15623; https://doi.org/10.3390/molecules181215613
Received: 28 October 2013 / Revised: 8 December 2013 / Accepted: 10 December 2013 / Published: 13 December 2013
In this article we describe a new methodology for the total synthesis of 3,4-unsubstituted coumarins from commercially available starting materials. Six examples were prepared, including five naturally occurring coumarins—7-hydroxy-6,8-dimethoxy-coumarin (isofraxidin), 7-hydroxy-6-methoxycoumarin (scopoletin), 6,7,8-trimethoxy-coumarin, 6,7-dimethoxycoumarin (scoparone), and 7,8-dihydroxycoumarin (daphnetin) and one synthetic coumarin, 7-hydroxy-6-ethoxycoumarin. Moreover, five important o-hydroxybenzaldehyde intermediates were also obtained, namely 2,4-dihydroxy-3,5-dimethoxybenzaldehyde, 2,4-dihydroxy-5-methoxybenzaldehyde, 5-ethoxy-2,4-dihydroxy-benzaldehyde, 2-hydroxy-3,4,5-trimethoxybenzaldehyde, and 2-hydroxy-4,5-dimethoxy-benzaldehyde. The method developed herein involves just three or four steps and allows for the rapid synthesis of these important molecules in excellent yields. This is the first synthesis of 6,7,8-trimethoxycoumarin and 7-hydroxy-6-ethoxycoumarin. View Full-Text
Keywords: 3,4-unsubstituted coumarins; o-hydroxybenzaldehyde derivatives; 6,7,8-trimethoxycoumarin; 7-hydroxy-6-ethoxycoumarin 3,4-unsubstituted coumarins; o-hydroxybenzaldehyde derivatives; 6,7,8-trimethoxycoumarin; 7-hydroxy-6-ethoxycoumarin
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MDPI and ACS Style

Gao, W.; Li, Q.; Chen, J.; Wang, Z.; Hua, C. Total Synthesis of Six 3,4-Unsubstituted Coumarins. Molecules 2013, 18, 15613-15623.

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