Utilization of the Intramolecular Cycloaddition-Cationic π-Cyclization of an Isomuenchnone Derivative for the Synthesis of (±)-Lycopodine was written by Padwa, Albert;Brodney, Michael A.;Marino, Joseph P. Jr.;Sheehan, Scott M.. And the article was included in Journal of Organic Chemistry in 1997.Application In Synthesis of 3-(3,4-Dimethoxyphenyl)propan-1-ol This article mentions the following:
A new annulation sequence leading to the tetracyclic skeleton of the Lycopodium family of alkaloids is effected by using the tandem cycloaddition-cationic π-cyclization reaction of an isomuenchnone dipole as the key strategic element. Synthesis of the required α-diazo imide precursor involved treating 5-methylcyclohex-2-en-1-one with the organocopper reagent derived from 3-methoxybenzyl chloride in the presence of chlorotrimethylsilane. Ozonolysis of the resulting silyl enol ether followed by a Wittig reaction and conversion to the desired α-diazo imide was carried out using standard malonylacylation and diazotization procedures. Treatment of the α-diazo imide with rhodium(II) perfluorobutyrate afforded a transient 1,3-dipole which subsequently cycloadded across the tethered π-bond. The resulting cycloadduct I was treated with BF3·2AcOH to give a rearranged tetracyclic compound derived from a Pictet-Spengler-type cyclization of an N-acyliminium ion. The rearranged product was subsequently converted into a key intermediate II previously used for the synthesis of (±)-lycopodine. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Application In Synthesis of 3-(3,4-Dimethoxyphenyl)propan-1-ol).
3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Application In Synthesis of 3-(3,4-Dimethoxyphenyl)propan-1-ol
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem