13-cis-retinoic acid, Isotretinoin, Ro-43780, Sotret, Amnesteem, Claravis, Roacutan, Roaccutan, Roaccutane, Accutane

合成路线:The formylation of the beta-ionone (I) with methyl formate and NaOMe gives the enol (II),which by reaction with methanol and H2SO4 yields the dimethylacetal (III).The reaction of (III) with methylenetriphenylphosphorane (IV) affords the methylene compound (V),which is treated with formic acid to provide the aldehyde (VI).The condensation of (VI) with isopropylidenemalonic acid dimethyl ester (VII) by means of NaOH gives the polyenic malonic acid (VIII) as a mixture of isomers that is separated by crystallization in ethyl ether to yield the desired all-trans-isomer (IX).Finally,this malonic acid is selectively monodecarboxylated by means of refluxing 2,6-dimethylpyridine to afford the target (E,E,E,Z)-isomer.

参考文献标题:Stereoselective synthesis of 13 E retinoic and 13 Z retinoic acids via a new intermediate compound,C-15 beta-methylenealdehyde
文献作者:Valia,A.; et al.
参考来源:Tetrahedron 2000,56(37),7211


合成路线:The reaction of vinyl-beta-ionol (I) with triphenylphosphonium bromide (II) in ethanol gives the corresponding phosphonium salt (III),which is condensed through a Wittig reaction with cis-beta-formylcrotonic acid (IV) by means of sodium ethoxide in ethanol to afford a mixture of cis-2-cis-4-vitamin A acid (V) and the desired product.Finally,compound (V) is isomerized bv irradiation with diffuse light in ether in the presence of iodine.
参考文献标题:Synthesis of cis-2,cis-4-vitamin A by a Wittig condensation
文献作者:Garbers,C.F.; et al.
参考来源:J Chem Soc 1968,(16),1982-83


产品链接: CAS No. 4759-48-2››

产品链接: CAS No.13497-05-7››