Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 16, Issue 18, Pages 3376-3381Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob00567b
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Funding
- National Natural Science Foundation of China [81373277]
- International Cooperative Program of the Chinese Academy of Sciences [GJHZ1622]
- Key Program of the Frontier Science of the Chinese Academy of Sciences [160621]
- Shanghai Commission of Science and Technology [16XD1404600, 14431905300, 14431900400]
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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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