59699-82-0Relevant articles and documents
Stereocontrolled synthesis of 13-substituted retinoic acids by palladium-catalyzed coupling reaction of alkenyl stannane with vinyl triflate
Wada,Fukunaga,Ito
, p. 800 - 802 (2007/10/03)
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.
Base-catalyzed isomerization of retinoic acid. Synthesis and differentiation-inducing activities of 14-alkylated all-trans-, 13-cis-, and 20,14-retro-retinoic acids
Tanaka,Kagechika,Kawachi,Fukasawa,Hashimoto,Shudo
, p. 567 - 572 (2007/10/02)
Retinoic acid (1) is isomerized regioselectively by excess amounts of lithium diisopropylamide (LDA) to give 20,14-retro-retinoic acid (3). Alkylation of the intermediate dianion of retinoic acid gave 14-alkylated derivatives of 3. By isomerization of the alkylated retro isomers under basic conditions, several 14-alkyl-all-trans- and -13-cis-retinoic acids were synthesized. The retinoidal activities of these derivatives were examined, based on the ability to induce differentiation of human promyelocytic leukemia cell line HL-60. 20,14-retro-Retinoic acid (3) is 1/50 as active as retinoic acid (1). Although 14-methyl-20,14-retro-retinoic acid (4) is as active as 3, the introduction of a 14-methyl group into all-trans- and 13- cis-retinoic acid resulted in decreased activity. Introduction of bulkier alkyl groups at the C-14 position caused the disappearance of the activity.
Synthesis of New Aromatic Retinoid Analogues by Low-Valent Titanium Induced Reductive Elimination
Solladie, Guy,Girardin, Andre,Lang, Gerard
, p. 2620 - 2628 (2007/10/02)
The low-valent titanium reductive elimination reaction, already applied to the stereospecific synthesis of vitamin A and 13-cis-retinol, was used to prepare several retinoic acid analogues in the all-trans configuration or in the 13-cis configuration.This highly stereospecific trans-diene formation allowed an improved synthesis of the title compounds without any purification of the intermediates before the final stage.
