184637-85-2

Upstream product

• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 184637-80-7 6-ethoxy-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl trifluoromethanesulfonate 
• 184637-78-3 6-ethoxy-1-(toluene-4-sulfonyl)-piperidin-2-one 
• 39662-64-1 6-ethoxypiperidin-2-one 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 189505-73-5 [6-Ethoxy-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydro-pyridin-2-yl]-methanol 
• 184637-86-3 2-Ethoxy-1-(toluene-4-sulfonyl)-6-(2-trimethylsilanyl-ethoxymethoxymethyl)-1,2,3,4-tetrahydro-pyridine 

Relevant academic research and scientific papers

Total synthesis of desoxoprosophylline: Application of a lactam-derived enol triflate to natural product synthesis

The total synthesis of desoxoprosophylline 1 from a piperidinone-derived enol triflate 8 has been realized and is one of the first applications of such lactam-derived triflates to natural product synthesis. Palladium-catalyzed methoxycarbonylation of 8 followed by 1,2-reduction and protection introduces the required C2 hydroxymethyl group, affording 10. The C3 hydroxy function is stereoselectively added by a novel N-tosylenamide hydroboration (de 88%), and the final C6 dodecyl chain is incorporated with complete stereocontrol, in a single step, via an N-tosyliminium ion-allylsilane coupling. Deprotection gives the natural product in an efficient 7.5% yield over nine steps.

Synthesis and reactivity of pyrrolidinone- and piperidinone-derived enol triflates

A high yielding route to cyclic lactam-derived enol triflates is given along with a study of the structural features necessary for such triflates to be of useful thermal stability. Some Pd(0)-mediated coupling reactions are disclosed as well as the first