Molecules p. 15613 - 15623 (2013)
Update date:2022-08-05
Topics:
Gao, Wenqing
Li, Qingyong
Chen, Jian
Wang, Zhichao
Hua, Changlong
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-dimethoxycoumarin (isofraxidin), 7-hydroxy-6-methoxycoumarin (scopoletin), 6,7,8-trimethoxycoumarin, 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- dihydroxybenzaldehyde, 2-hydroxy-3,4,5-trimethoxybenzaldehyde, and 2-hydroxy-4,5-dimethoxybenzaldehyde. 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.
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Doi:10.1016/j.tetlet.2009.05.031
(2009)Doi:10.1002/asia.200800249
(2009)Doi:10.1021/ja00185a039
(1989)Doi:10.1002/chem.201504780
(2016)Doi:10.1039/b903516h
(2009)Doi:10.1016/S0040-4020(01)93609-9
(1978)