304466-91-9

Upstream product

• 180736-80-5 (4E)-3-methylene-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-4-pentenal 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 85458-25-9 5,5-dimethoxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-1-en-3-one 
• 180736-86-1 1-hydroxy-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-1,4-dien-3-one 
• 180736-79-2 2-[3-(2,2-dimethoxy-ethyl)-buta-1,3-dienyl]-1,3,3-trimethylcyclohexene 
• 79-77-6 (E)-β-ionone 

Relevant academic research and scientific papers

Synthesis of new 9-methylene analogs of retinoids

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.

Syntheses of new 9- and 13-methylene isomers of retinal

Syntheses of new 9- and 13-methylene isomers of retinal via the '9-methylene-C-18 ketone' 1 or 'C-18 ketone' 2 are reported. (C) 2000 Published by Elsevier Science Ltd.