Abstract
Herein, a convergent, practicable and first total synthesis of the natural product, (±)-methyl salvianolate A, is reported. The key features of the approach are the use of a Horner–Wadsworth–Emmons reaction and the protection of multiple hydroxyls using silyl protecting groups. The employment of the readily removable silyl protecting groups allows the synthesis of (±)-methyl salvianolate A and its derivatives on a reasonably large scale.
Highlights
Traditional Chinese medicines, which are rich in bioactive natural products, and are widely used in China and Asian countries, play a significant role in the treatment of several diseases.The Chinese herb Danshen from the Chinese Pharmacopoeia has been widely used, for example, to treat cerebro-cardiovascular, gynecologic, and digestive diseases [1]
The significant pharmacological activity may be attributed to the novel biological active components present in Danshen
To the the best best of of our our knowledge, most of of the that are structurally similar to involve the use of methyl ether that are structurally similar to (±)-methyl salvianolate A involve the use of methyl ether protecting protecting groups, which which effectively effectively avoids avoids the the influence influence of of the the phenol phenol groups groups during during the the synthesis
Summary
Traditional Chinese medicines, which are rich in bioactive natural products, and are widely used in China and Asian countries, play a significant role in the treatment of several diseases.The Chinese herb Danshen from the Chinese Pharmacopoeia has been widely used, for example, to treat cerebro-cardiovascular, gynecologic, and digestive diseases [1]. Salvianolate A showed considerable biological properties, including antioxidant [3,4,5,6], cardio- protective [7,8], antiplatelet, and antithrombotic activities [9], as well as reversing the paclitaxel resistance and inhibiting tumor migration and invasion of human breast cancer [10]. These multiple pharmacological effects attracted numerous pharmacological groups to devote their research efforts toward investigating salvianolate A. Despite the numerous biological studies conducted on salvianolate A, only four total syntheses of salvianolate A [12,13,14,15] and one for salvianolate F [16], which possesses a similar
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