96839-29-1

Usage

InChI:InChI=1/C18H16O4/c1-9-8-22-17-11-5-6-12-10(4-3-7-18(12,2)21)14(11)16(20)15(19)13(9)17/h5-6,8,21H,3-4,7H2,1-2H3

Upstream product

• 930-68-7 cyclohexenone 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 140709-89-3 2-vinylcyclohex-2-en-1-one 
• 113297-21-5 4,5-dihydro-3-methylbenzo[1,2-b]furan-4,5-dione 
• 124292-44-0 1-methyl-2-vinylcyclohex-2-en-1-ol 
• 7182-21-0 5-hydroxy-3-methylbenzo<1.2-b>furan 

Downstream Products

• 96894-91-6 (+)-(3R,4S)-tanshindiol B 
• 97465-70-8 tanshindiol B 
• 96839-30-4 (+)-(3S,4S)-tanshindiol C 
• 96839-30-4 tanshindiol C 
• 96839-30-4 (±)-tanshindiol C 
• 77769-21-2 1,6-dimethyl-8,9-dihydrophenanthro[1,2-b]furan-10,11-dione 

Relevant academic research and scientific papers

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 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.