scholarly journals Synthesis of 2-O-(4-Coumaroyl)-3-(4-hydroxyphenyl)lactic Acid, an Important Intermediate of Rosmarinic Acid Biosynthesis.

2001 ◽  
Vol 49 (12) ◽  
pp. 1644-1646 ◽  
Author(s):  
Michiyo MATSUNO ◽  
Akito NAGATSU ◽  
Yukio OGIHARA ◽  
Hajime MIZUKAMI
2008 ◽  
Vol 38 (2) ◽  
pp. 189-197 ◽  
Author(s):  
Guo-Qian Xu ◽  
Ju Chu ◽  
Ying-Ping Zhuang ◽  
Yong-Hong Wang ◽  
Si-Liang Zhang

2013 ◽  
Vol 48 (7) ◽  
pp. 1474-1482 ◽  
Author(s):  
Qingli Zhang ◽  
Mindy M. Brashears ◽  
Zhimin Yu ◽  
Jiaoyan Ren ◽  
Yinjuan Li ◽  
...  

2017 ◽  
Vol 51 (2) ◽  
pp. 175-190 ◽  
Author(s):  
L. S. Gordeev ◽  
A. V. Koznov ◽  
A. S. Skichko ◽  
Yu. L. Gordeeva

1997 ◽  
Vol 75 (12) ◽  
pp. 1783-1794 ◽  
Author(s):  
David E. Bogucki ◽  
James L. Charlton

The synthesis of (S)-(−)-rosmarinic acid (30) in 9% overall yield is described. The synthesis was achieved by a convergent route in which 3-(3′,4′-dihydroxyphenyl)-(S)-lactic acid (23) and caffeic acid (25), both appropriately protected, were coupled to produce a pentaallyl precursor 29, which was then deprotected to give (S)-(−)-rosmarinic acid (30). A triallyl derivative 35 was similarly prepared and converted to (+)-rabdosiin (41) and its (1R,2S) isomer (42) via a biomimetic oxidative free radical coupling–cyclization followed by deallylation. The coupling–cyclization gave a ratio of rabdosiin diastereomers unlike that found in nature. A preliminary study showed that methyl (R)-mandelyl sinapate (15) could be dimerized diastereoselectively to give a 1,2-trans thomasidioate diester (16). Keywords: rabdosiin, rosmarinic acid, lignan, oxidative coupling.


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