Jun Mo Gil

The stereoselective synthesis of cyclopropylphosphonate analogs of nucleotides

Abstract 1-Alkenylphosphonic acid derivatives of purines have been proven to exhibit significant antiviral activity among these series of compounds. Here we disclose the stereoselective synthesis of the constrained analogs of 1-alkenylphosphonate derivatives of purines via intramolecular epoxide opening reaction of γ,δ-epoxyalkanephosphonates with subsequent Mitsunobu coupling reactions with purine bases.

One-Pot Synthesis of 1-Alkynylphosphonates

Abstract 1-Alkynylphosphonates 3 are prepared in a one-pot procedure from diethyl phosphorochloridates 2 and alkynyllithiums 1, which are readily generated by the reaction of 1-alkynes with n-BuLi.

Regioselective alkylation and olefination of allylic carbanion stabilized by two different heteroatoms: phosphorus and silicon

Abstract Treatment of allylphosphonate with LiHMDS, followed by successive addition of chlorotrimethylsilane and carbonyl reagent, afforded dienylsilanes in good yields. 3-Substituted dienylsilanes were obtained by alkylation and olefination of allylic carbanion of 3-trimethylsilylallylphosphonates.

One pot synthesis of mono- and spirocyclic α-phosphonato-α,β-unsaturated cycloenones

Abstract A one pot ozonolysis/intramolecular aldol condensation(with the aid of TsOH and Et 3 N as catalysts) of β-keto-ω-alkenylphosphonates provided the α-phosphonato-α,β-unsaturated cycloenone with good yields.

A concise synthesis of the sex pheromone of Phtheochroa cranaodes (Lepidoptera: Tortricidae)

The female sex pheromone (3E,5Z)-3,5-dodecadienyl acetate of Phtheochroa cranaodes was regio- and stereo-selectively synthesized using electrophilic trimethylchlorostannane-induced rearrangement of lithium 1-octynylborate as the main process

A Facile Synthesis of Diethyl 1-Formylalkane Phosphonates via Ozonolysis of 1-Alkyl Allylic Phosphonates

Abstract The 1-formylalkanephosphonates were obtained by the ozonolysis of the corresponding 1-alkylated allylphosphonates, which had been previously prepared by treatment with n-BuLi, followed by addition of alkyl halides.

Stereoselective synthesis of ketene telluroacetals viahydrozirconation of acetylenic tellurides

Hydrozirconation of acetylenic tellurides 1 gives organozirconium(IV) complexes 2, which are trapped with tellurenyl iodides to afford ketene telluroacetals 3.