58526-49-1

Upstream product

• 160096-44-6 α-ionone 
• 75-16-1 methylmagnesium bromide 
• 419550-09-7 dimethyl 2-[(2E)-3-(dimethylamino)-1-methyl-2-propenylidene]malonate 
• 220212-07-7 (2Z,4E)-5-iodo-3-methylpenta-2,4-dienoic acid 
• 180736-83-8 6-((E)-5,5-Dimethoxy-3-methylene-pent-1-enyl)-1,5,5-trimethyl-cyclohexene 
• 180736-82-7 (E)-5,5-Dimethoxy-1-(2,6,6-trimethyl-cyclohex-2-enyl)-pent-1-en-3-one 
• 180736-84-9 (E)-3-Methylene-5-(2,6,6-trimethyl-cyclohex-2-enyl)-pent-4-enal 
• 22035-53-6 dimethyl isopropylidenemalonate 
• 180736-85-0 2-[(2E,4E,6E)-1,5-Dimethyl-7-(2,6,6-trimethyl-cyclohex-2-enyl)-hepta-2,4,6-trienylidene]-malonic acid 

Relevant academic research and scientific papers

Stereoselective synthesis of trienoic acids: Synthesis of retinoic acids and analogues

Stereoselective construction of conjugated trienoic acids was achieved through two successive Stille reactions, the first step consisting of the coupling of (E)-1,2-bis(tributylstannyl)ethene and tributylstannyl (Z)- or (E)-3-iodoalk-2-enoates. Two different routes were used for the second step: (1) cross-coupling of the stannyldienoic acid reagents and vinyl iodides, or (2) cross-coupling of vinylstannane reagents and the tributylstannyl 5-iodopenta-2,4-dienoates generated by iododestannylation of stannyldienes. Vinylstannanes synthesized by stannylmetalation of the Negishi dienyne derived from β- or α-ionone and safranal thus provided access to stereodefined retinoic acids. Some retinoid and yne analogues were also prepared by Sonogashira coupling. Georg Thieme Verlag Stuttgart.

New, regioselective, one-pot synthesis of (all-E)-retinoic acid and analogues from enaminodiester synthons

A one-pot synthesis of (all-E)-retinoic acid and related compounds from new enamino diester synthons is described. The enamino diesters was produced nearly quantitatively from methyl propylidene- and isopropylidenemalonate and DMF-DMA. This easy process allowed retinoic acid to be produced in 1 d and appeared advantageous to current industrial syntheses. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

Stereoselective synthesis of 13Z retinoic acids via β-methylenealdehydes as synthons

A stereoselective synthesis of 13Z retinoic acids via β-methylenealdehydes is described. In methylene-de-oxo-bisubstitution reactions (Knoevenagel, Stobbe, etc.), these new synthons produce stereoselectively E olefins. Hence, a synthesis of 13Z retinoic acids is described, via a stereospecific monodecarboxylation of carboxy-14-retinoic acids.