96839-30-4Relevant articles and documents
Total synthesis of (±)-tanshinol B, tanshinone I, and (±)-tanshindiol B and C
Wang, Fan,Yang, Hong,Yu, Shujuan,Xue, Yu,Fan, Zhoulong,Liang, Gaolin,Geng, Meiyu,Zhang, Ao,Ding, Chunyong
, p. 3376 - 3381 (2018/05/23)
A concise and efficient approach was established for the divergent total synthesis of (±)-tanshindiol B and C and tanshinone I from a ubiquitous ene intermediate in 1-2 steps. This critical intermediate was derived from (±)-tanshinol B, which was synthesized in 50% overall yield over 3 steps using an ultrasound-promoted cycloaddition as a key step. Compared to a previously reported strategy, our approach is more step-economic, thus greatly improving the synthetic efficiency. The bioactivity evaluation indicates that the diol stereochemistry of the tanshidiols has an impact on the EZH2 inhibitory activity.
Asymmetric Syntheses of Salvia miltiorrhiza Abietanoid o-Quinones: Methyl Tanshinonate, Tanshinone IIB, Tanshindiol B, and 3-Hydroxytanshinone
Haiza, Mohammed,Lee, Junning,Snyder, John K.
, p. 5008 - 5013 (2007/10/02)
The Diels-Alder reaction of 3-methyl-4,5-benzofurandione with vinylcyclohexene derivatives using either high-pressure or ultrasound promotion has led to the asymmetric synthesis of methyl tanshinonate, tanshinone IIB, tanshindiol B, and 3-hydroxytanshinone.The abietanoid diterpenes are active constituents of the Chinese traditional medicine, Dan Shen, prepared from the roots of Salvia miltiorrhiza Bunge.As a result, the absolute stereochemistry of these natural products has been assigned: (-)-(4S)-methyl tanshinonate, (-)-(4S)-tanshinone IIB, (-)-(3S,4R)-tanshindiol B, and (+)-(3S)-3-hydroxytanshinone.