353744-04-4

Upstream product

• 25576-25-4 (3E,5E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3,5-hexadien-1-yne 
• 134405-82-6 ethyl (E)-3-<<(trifluoromethyl)sulfonyl>oxy>-2-heptenoate 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 141-97-9 ethyl acetoacetate 

Relevant academic research and scientific papers

Preparation and biological activity of 13-substituted retinoic acids

13-Demethyl or 13-substituted all-E- and 9Z-retinoic acids were synthesized using a palladium-catalyzed coupling reaction of enol triflates and tributylstannylolefins. Their biological activities were then measured. The 13-ethyl analogs exhibited approximately one-half of the antiproliferative and differentiation-inducing activity of ATRA in HL-60 cells. In contrast, in the 9Z-derivatives, all analogs, except for the 13-butyl derivatives, showed apoptosis-inducing activity.

Stereocontrolled synthesis of 13-substituted retinoic acids by palladium-catalyzed coupling reaction of alkenyl stannane with vinyl triflate

A novel method for the stereoselective synthesis of all-E-, 13Z- and 9Z- retionic acid esters was developed by palladium-catalyzed cross coupling reactions of tetraenyl stannanes with E- or Z-vinyl triflates in good yields. Applying this methodology, 13-substituted all-E- and 9Z- retinoic acids were prepared in satisfactory yields.