Shigeaki Suzuki

Preparation of substituted benzoyltrimethylsilanes by the palladium-catalyzed silylation of substituted benzoyl chlorides with hexamethyldisilane

Abstract A direct preparative route to benzoyltrimethylsilane has been found by the reaction of benzoyl chloride with hexamethyldisilane in the presence of a specified palladium(II) complex as catalyst.

Synthesis of mammalian dolichols from plant polyprenols

Abstract Both natural (S)- and unnatural (R)-mammalian dolichols were synthesized for the first time from the mixture of novel polyprenols isolated from Ginkgo biloba .

Stereochemical consequence in the elimination of β-hydroxyalkylsilanes: Stereoselective formation of (Z)- and (E)-alkylidene-γ-butyrolactones

Titanium(IV) chloride-mediated reaction of 4,5-dihydro-2-(trimethylsiloxy)-3-(trimethylsilyl)furan (1a) with acetaldehyde gave diastereomerically pure (3S*, 1′R*)-4,5-dihydro-3-(1′hydroxyethyl)-3-(trimethylsilyl)-2(3H)furanone (2a), which afforded selectively either (Z)- or (E)-α-ethylidene-γ-butyrolactone (3a) under proper conditions. Facile isomerization of 2a into diastereomerically pure (3S*, 1′R*)-4,5-dihydro-3-&{1′-(trimethylsiloxy)ethyl}-2(3H)furanone (4) suggests an intriguing stereochemical outcome from 2a to (E)-3a via an enolate of 4.

Regio- and Stereoselective Oxidation of Ene-Type Chlorinated Olefins

Abstract Regio- and stereoselective oxidation of ene-type chlorinated olefins has been achieved by using potassium 2-propanenitronate as an oxidant and tetrakis(triphenylphosphine)palladium as a catalyst.

New approach to polyisoprenepolyols possessing glycerol termini by using a highly oxygenated C5-unit

Abstract Polyisoprenepolyols possessing glycerol termini have been synthesized by using 4-(1,2-epoxy-1-methylethyl)-2-phenyl-1,3-dioxolane as a novel highly oxygenated C5-unit.

New diene formation by ene-type chlorination and palladium catalyzed dehydrochlorination: Synthesis of citral from diprenyl ether

Abstract Synthesis of citral from diprenyl ether is achieved by new diene forming reaction which consists of ene-type chlorination and palladium catalyzed dehydrochlorination.

A Convenient Preparative Route to 1,2-Epoxy-3-Methyl-3-Butene Via Ene-Type Chlorination

Abstract 1,2-Epoxy-3-methyl-3-butene has been synthesized from prenyl acetate by using ene-type chlo-rination.

Synthesis of Polyisoprenepolyols Having Multiple Tertiary Hydroxy Moieties Via Hydromagnesation

Abstract Synthesis of polyisoprenepolyols possessing multiple tertiary hydroxy moieties has been achieved efficiently by using hydromagnesation.

Synthesis of Unsaturated Nitriles from Trisubstituted Olefins Via Ene-Type Chlorination

Abstract Unsaturated nitriles have been synthesized from trisubstituted olefins via ene-type chlorination and regioselective substitution with cyanide ion followed by double bond migration.

New Synthetic Method for Bicyclic Compounds Through a Sequence of Ene-Type Chlorination, Palladium Catalyzed Dehydrochlorination, and Intramolecular Diels-Alder Reaction

Abstract A sequence of ene-type chlorination, palladium catalyzed dehydrochlorination, and the intramolecular Diels-Alder reaction afforded a new method for conversion of prenyl derivatives into bicyclic compounds.