25576-26-5

Upstream product

• 624-67-9 Propargylic aldehyde 
• 66556-69-2 (E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1-buten-3-yltriphenylphosphonium bromide 
• 74352-12-8 9-(2-propynyl)-β-ionyl acetate 
• 54226-17-4 (2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal 
• 79-77-6 (E)-β-ionone 
• 74352-11-7 6-(2-methyl-6,6-dimethylcyclohex-1-en-1-yl)-3-methylhex-1-ene-5-yne-3-ol 
• 22029-76-1 beta-ionol 
• 303779-99-9 (E)-2-(2,6,6-trimethylcyclohexen-1-yl)-ethenyl (trifluoromethyl)sulfonate 
• 3917-40-6 (2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienol 

Downstream Products

• 1360895-27-7 (Z)-3-bromo-4-methyl-5-((2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienylidene)furan-2(5H)-one 
• 1360895-20-0 (Z)-3-(4-methoxyphenyl)-4-methyl-5-((2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienylidene)furan-2(5H)-one 
• 302-79-4 9-cis-retinoic acid 
• 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 
• 353744-07-7 ethyl (2E,4E,6Z,8E)-7-methyl-3-propyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 353744-06-6 ethyl (2E,4E,6Z,8E)-3-ethyl-7-methyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 353744-08-8 ethyl (2E,4E,6Z,8E)-3-butyl-7-methyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 86708-67-0 ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate 

Relevant academic research and scientific papers

Carboxylate-directed tandem functionalisations of α,β- dihaloalkenoic acids with 1-alkynes: A straightforward access to (Z)-configured, α,β-substituted γ-alkylidenebutenolides

An easy and mild copper(I)-catalysed lactonisation of readily available (E)-2,3-dihalopropenoic acid derivatives regio- and stereoselectively leads to rarely described (Z)-3-halo-5-ylidene-5H-furan-2-ones. These compounds are subsequently able to undergo classical Pd-catalysed cross-coupling reactions, providing 3-substituted and 3,4-disubstituted 5-ylidene-5H-furan-2-ones (see scheme).

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.

10-Mono-, 11-mono-, 12-mono and 11,12-dideuteroretinal

The 11-mono and 12-mono- and 11,12-dideuteroretinal (in the all-trans, 9-cis, 11-cis and 13-cis form) with > 98percent chemical purity and > 95percent mono- and dideuterium incorporation were prepared using the same scheme for all three compounds.The all-