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Issue 18, 2018
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Total synthesis of (±)-tanshinol B, tanshinone I, and (±)-tanshindiol B and C

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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.

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

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Publication details

The article was received on 07 Mar 2018, accepted on 03 Apr 2018 and first published on 04 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00567B
Citation: Org. Biomol. Chem., 2018,16, 3376-3381
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    Total synthesis of (±)-tanshinol B, tanshinone I, and (±)-tanshindiol B and C

    F. Wang, H. Yang, S. Yu, Y. Xue, Z. Fan, G. Liang, M. Geng, A. Zhang and C. Ding, Org. Biomol. Chem., 2018, 16, 3376
    DOI: 10.1039/C8OB00567B

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