124292-44-0

Upstream product

• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 75-16-1 methylmagnesium bromide 
• 140709-89-3 2-vinylcyclohex-2-en-1-one 
• 930-68-7 cyclohexenone 
• 141237-72-1 1,4-dioxa-6-formylspiro[4,5]dec-6-ene 
• 23155-97-7 1-Vinyl-2-methylcyclohexene 
• 118949-96-5 2-vinylcyclohex-2-en-1-one ethylene glycol ketal 
• 70156-98-8 6-bromo-1,4-dioxaspiro[4,5]dec-6-ene 
• 50870-61-6 2-bromocyclohex-2-en-1-one 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 403694-37-1 3-methoxy-3-methyl-2-vinylcyclohexene 
• 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 
• 568-73-0 Tanshinone I 
• 96839-29-1 6-hydroxy-1,6-dimethyl-6,7,8,9-tetrahydrophenanthro[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.

Heteroatom influence on the π-facial selectivity of Diels-Alder cycloadditions to 1-oxa-4-thia-6-vinylspiro[4.5]dec-6-ene, 3-Methoxy-3-methyl-2-vinylcyclohexene, and 3-methoxy-2-vinylcyclohexene

The facial selectivities of the Diels-Alder cycloadditions of several dienophiles to the title substrates were studied. The observed selectivities are interpreted as a consequence of the relative steric interactions offered by the substituents. The addition of dimethylacetylene dicarboxylate (DMAD) is influenced by the electrostatic repulsion arising from the interaction of an electron pair orbital on the acetal oxygen and the orthogonal π-orbital of the acetylene unit in DMAD in the syn-to-oxygen addition of the latter. This repulsion is offset on coordination of Li+ to the said oxygen electron pair orbital, and the addition thus proceeds syn to oxygen. The enhanced and accelerated syn-to-oxygen addition in lithium perchlorate in nitromethane is interpreted as a consequence of the coordination of Li+ to both the acetal oxygen and a heteroatom in the dienophile that brings them in close proximity to facilitate a reaction. The Li+-oxygen combination, however, also exerts some steric effect that results in reduced syn-to-oxygen addition of dienophiles having large substituents such as N-phenylmaleimide.

AN EFFICIENT STEREOSELECTIVE SYNTHESIS OF Z-2-(2-METHYLENE CYCLOHEXYLIDENE)ETHANOL BY THE PHOTOSENSITIZED OXYGENATION OF 1-VINYLCYCLOHEXENE. A MODEL FOR RING A OF CALCITRIOL

The reaction of singlet oxygen with the vinylcyclohexene leads to an endoperoxide which is a model for a possible route to ring A of calcitriol.