2. Academic Validation
  3. Total synthesis of (±)-tanshinol B, tanshinone I, and (±)-tanshindiol B and C

Total synthesis of (±)-tanshinol B, tanshinone I, and (±)-tanshindiol B and C

  • Org Biomol Chem. 2018 May 9;16(18):3376-3381. doi: 10.1039/c8ob00567b.
Fan Wang 1,  Hong Yang,  Shujuan Yu,  Yu Xue,  Zhoulong Fan,  Gaolin Liang,  Meiyu Geng,  Ao Zhang,  Chunyong Ding
Affiliations

Affiliation

  • 1 Nano Science and Technology Institute, University of Science and Technology of China, Suzhou 215123, China.
PMID: 29670981 DOI: 10.1039/c8ob00567b
Abstract

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.

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