Total Synthesis of Tanshinone I

Abstract

A novel total synthesis of tanshinone I (1) via the intermediate 3-hydroxy-8-methyl-1,4-phenanthrenedione (8) is described. The low overall yields and the use of expensive reagents in the synthesis process were minimized by the use of the Diels-Alder reaction to directly construct the 1,4-phenanthrenedione scaffold, providing tanshinone I (1) in only three steps.

Salvia miltiorrhizaBurge (Danshen): a golden herbal medicine in cardiovascular therapeutics

“…The possible therapeutic role of Danshen components for the treatment of chronic heart diseases related to cardiac remodeling must be further elucidated. Future directions of cardiovascular research involving Danshen include the following: (1) use of the total synthesis of bioactive components of Danshen for the purpose of cardiovascular therapeutics as an alternative to obtaining purified compounds from the medicinal plant, such as the recently described synthesis of tanshinone I [308] ; (2) use of a systems biology approach, such as RNA-sequencing [309] , or networkbased pharmacological research [310] to understand the gene regulation profile of each individual compound at the genomewide level; and (3) elucidation of the therapeutic effects of Danshen components in cardiovascular aging, which is a common basis for all major cardiovascular and metabolic diseases. Overall, Danshen and its bioactive constituents represent an invaluable source for small-molecule cardiovascular drug discovery.…”

Research and Development of Natural Product Tanshinone I: Pharmacology, Total Synthesis, and Structure Modifications

“… Wu et al (2017) used 2-methylstyrene ( 10 ) and 2-methoxy-1,4-benzoquinone ( 11 ) as raw materials to synthesize tanshinone I ( Figure 4 ). Compounds 10 and 11 underwent the Diels-Alder reaction in toluene to yield compound 12 .…”

Qualitative and quantitative determination of YiXinShu Tablet using ultra high performance liquid chromatography with Q Exactive hybrid quadrupole orbitrap high-resolution accurate mass spectrometry

“…Overall, a total of 105 compounds were identified or tentatively characterized from YXS Tablet. These compounds include 25 phenanthraquinones, 11 lactones, 19 lignans, 24 acids, and 26 other compounds [13][14][15][16][17][18][19][20][21][22]. Their retention times, molecular formulas, high-resolution MS data, and high-resolution MS 2 fragment ions are summarized in Table 1.…”