868773-11-9Relevant academic research and scientific papers
Synthesis of new 9-methylene analogs of retinoids
Valla, Alain,Andriamialisoa, Zo,Cartier, Dominique,Labia, Roger,Potier, Pierre
, p. 2363 - 2369 (2005)
We report herein a series of syntheses that provides diverse structural modifications of the side-chain of retinoids to obtain new compounds with potential use in anticancer therapy. Starting from a β-methylenealdehyde synthon, we have synthesized a series of new 9-methylene-13-desmethyl-14-methyl analogs and a series of 9-methylene-11-desmethyl trienic homologs. For the first series, the condensation of the C-15 β-methylenealdehyde with the anion of ethyl 4-(diethoxyphosphoryl)-2E-methylbut-2-enoate led to the 7E,11E,13E-ester. This gave the desired aldehyde by a reduction into the corresponding alcohol (DIBAL-H) and subsequent oxidation by MnO2. For the second series, the reaction of the C-15 β-methylenealdehyde with the anions of ethyl diethoxyphosphorylacetate, diethyl cyanomethylphosphonate, or diethyl 2-oxopropylphosphonate led to the C-17 ester, the C-17 nitrile, and the C-18 ketone, respectively. Copyright Taylor & Francis, Inc.
