76985-03-0Relevant articles and documents
A Highly Stereoselective Synthesis of 11Z-Retinal Using Tricarbonyliron Complex
Wada, Akimori,Fujioka, Naoko,Tanaka, Yukiko,Ito, Masayoshi
, p. 2438 - 2443 (2000)
A stereoselective synthesis of 11Z-retinal 2, which is the chromophore of visual pigment (rhodopsin), was accomplished from the β-ionylideneacetaldehyde-tricarbonyliron complex 3. The Peterson reaction of 3 using ethyl trimethylsilylacetate smoothly proce
Synthesis of (12,13-(13)C2)retinal and (13,14-(13)C2)retinal: a strategy to prepare multiple-(13)C-labeled conjugated systems
Groesbeek, M.,Rood, G. A.,Lugtenburg, J.
, p. 149 - 154 (2007/10/02)
(12,13-(13)C2)Retinal, (13,14-(13)C2)retinal, (19-(13)C)retinal and (20-(13)C)retinal (1) were prepared in a simple fashion in high yield via a consecutive strategy.The key step is the reaction of a N-methoxy-N-methylamide with an alkyllithium or a Grignard reagent.The preparation of the required N-methoxy-N-methylamide is discussed.In this scheme, only three commercially available (13)C-labeled starting materials (ethyl bromoacetate, acetonitrile and methyl iodide) are sufficient to construct retinals with any possible combination of (13)C labeling in the conjugated tail end.This strategy is applicable to the preparation of many other conjugated systems, such as retinoids, carotenoids and polyenes.
SYNTHETIC INVESTIGATIONS IN THE CHEMISTRY OF POLYENE COMPOUNDS. L. SYNTHESIS OF THE NITRILES AND HYDROXYNITRILES OF RETINOIC ACID
Zakharova, N. I.,Gutnikova, N. P.,Bekker, A. R.,Filippova, T. M.,Miropol'skaya, M. A.,Samokhvalov, G. I.
, p. 1870 - 1874 (2007/10/02)
Glycidonitrile was synthesized from 9-methyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-9,11-octadien-13-one and chloroacetonitrile by a modified Darzens reaction.Opening of the epoxide ring in the glycidonitrile gave 9,14-dihydroxy-9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-10,12-nonadiene-15-nitrile with a yield of 70percent calculated on the ketone.Partial dehydration of the latter gave 14-hydroxy-9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-8,10,12-nonatriene-15-nitrile - the key compound in the synthesis of the biologically active analog of the vitamin Ametabolite.The total dehydration of the dihydroxynitrile led to retinonitrile.