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

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 a...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018-05, Vol.16 (18), p.3376-3381
Main Authors: Wang, Fan, Yang, Hong, Yu, Shujuan, Xue, Yu, Fan, Zhoulong, Liang, Gaolin, Geng, Meiyu, Zhang, Ao, Ding, Chunyong
Format: Article
Language:English
Subjects:
Biological activity
Cycloaddition
Stereochemistry
Synthesis
Ultrasound
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Summary: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. A concise and efficient approach was established for the divergent total synthesis of (±)-tanshinol B, (±)-tanshindiol B, (±)-tanshindiol C, and tanshinone I in 17-50% overall yield over 3-6 steps.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob00567b