122135-98-2

Upstream product

• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 141-97-9 ethyl acetoacetate 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 17071-29-3 ethyl 3-oxo-5-phenylpentanoate 
• 100-39-0 benzyl bromide 

Downstream Products

• 353744-09-9 (2E,4E,6Z,8E)-7-Methyl-3-phenethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid ethyl ester 
• 353744-05-5 ethyl (2E,4E,6E,8E)-7-methyl-3-(2-phenyl)ethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 39806-16-1 ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate 
• 935254-77-6 5-phenyl-penta-2,3-dienoic acid ethyl ester 

Relevant academic research and scientific papers

Palladium-catalyzed elimination/isomerization of enol triflates into 1,3-dienes

Dying to be Dienes: Substituted 1,3-dienes were synthesized by the title reaction (see scheme; Tf=trifluoromethanesulfonyl). Preliminary studies support a mechanistically distinct pathway that involves an initial β-hydride elimination from a cationic vinyl palladium(II) intermediate, a subsequent regiospecific hydropalladation of the corresponding allene intermediate, and a final β-hydride elimination. Copyright

Stereoselective synthesis of acetoacetate-derived enol triflates

(Chemical Equation Presented) A highly stereoselective method for preparing (Z)- and (E)-enol triflates derived from substituted acetoacetate derivatives is described. The salient feature of this methodology is the use of Schotten-Baumann-type conditions

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.