Abstract
First total synthesis of the natural product salvianolic acid C, tournefolal and tournefolic acid A has been described. The key benzofuran skeletons are prepared via selective iodination and Sonogashira reaction.
Highlights
Salvia miltiorrhiza Bunge (Dan-shen) is widely used as a Chinese traditional medicine for the treatment of myocardial infarction, atherosclerosis, and thrombus.[1]
Liang et al.[5] have reported that salvianolic acid C (1) displays anti-proliferative activity against HepG2 cells with IC50 value of 20 M through apoptosis, and the mechanism is concerned with inhibition of tubulin polymerization
Salvianolic acid C (1), tournefolic acid A (3), and tournefolal (4) have substitutents at C-4, which are distinct from common natural neolignans having substitutents at C-5
Summary
Salvia miltiorrhiza Bunge (Dan-shen) is widely used as a Chinese traditional medicine for the treatment of myocardial infarction, atherosclerosis, and thrombus.[1]. Due to the importance of 2-phenyl-benzofuran derivatives, many methods for synthesis of these compounds have been developed.[10,11,12,13] salvianolic acid C (1), tournefolic acid A (3), and tournefolal (4) have substitutents at C-4, which are distinct from common natural neolignans having substitutents at C-5. The crude product was purified by recrystallization from DCM/PE to afford a white solid 4(benzyloxy)-3-hydroxy-benzaldehyde (4.4 g, 67%).
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