Sachihiko Isoe

Regiospecific synthesis of γ-hydroxybutenolide. Photosensitized oxygenation of substituted 2-trimethylsilylfuran

Abstract Regiospecific synthesis of substituted γ-hydroxybutenolide was accomplished by photosensitized oxygenation of 2-trimethylsilyl-furan derivatives, and chemoselective oxidation of furan ring having tri- and tetra-substituted olefins in the side chain was also achieved.

Electrochemical oxidation of organosilicon compounds. I: Oxidative cleavage of carbon-silicon bond in allylsilanes and benzylsilanes

Abstract Electrochemical oxidation of allylsilanes and benzylsilanes in the presence of alcohol, carboxylic acid, or water resulted in cleavage of the carbon-silicon bond and formation of the corresponding ether, ester, or alcohol, respectively.

Electrochemical oxidation of α-silylcarbamates1

Abstract α-Silyl group activates carbamates toward electrochemical oxidationwhich results in facile cleavage of carbon-silicon bond and regioselective introduction of methanol at α-carbon.

Total synthesis of manoalide and seco-manoalide

Abstract The first synthesis of manoalide and seco-manoalide from methyl 7,8-dihydro-β-ionylidene acetate was achieved in high yield by the new method utilizing regiospecific singlet oxygen oxidation of 3-alkenyl-5-trimethylsilylfuran to β-alkenyl-γ-hydroxybutenolide.

Oxidative fragmentation of γ-hydroxyalkyl stannanes stereospecific formation of (E) and (Z)-keto olefins

Abstract Treatment of γ-hydroxyalkyl stannanes with lead tetraacetate in refluxing benzene leads to the stereospecific formation of (E) and (Z)-keto olefins according to the stereochemistry of the starting materials in excellent yield.

Photoinduced DNA cleavage by designed molecules with conjugated ene-yne-ketene functionalities

Upon photoirradiation, diazoketone 1 was found to induce single strand cleavage of plasmid pBR322 DNA at concentration of 100 μM. Conjugate ene-yne moiety was essential for DNA-cleaving activities.

New one carbon homologation reagents utilizing electrochemical oxidation of organosilicon compounds

Abstract Phenylthio(trimethylsilyl)methane, phenylthiobis(trimethylsilyl)methane, methoxy(trimethylsilyl)methane, and methoxybis(trimethylsilyl)methane are deprotonated and the resulting anions are alkylated with electrophiles such as organic halides. The alkylation products are readily converted into the corresponding dimethyl acetals or methyl esters by electrochemical oxidation in methanol.

Highly efficient total synthesis of manoalide and seco-manoalide via Pd(0) catalyzed coupling of allyhalide with CO and 2-silyl-4-stannylfuran

Abstract Total synthesis of manoalide and seco-manoalide from an allylchlolide derivative was achieved by 6 steps in 56.4% overall yield by Pd(0) catalyzed coupling with CO and 2- trimethylsilyl-4-tributylstannylfuran followed by chemoselective oxidation of 2-trimethylsilylfuran with 1 O 2 .

Revisions of the absolute configurations of C-8 methyl groups in dehydroiridodiol, neonepetalactone, and matatabiether from Actinidia polygama miq

Abstract The absolute configurations of C-8 Me groups in dehydro-iridodiol, neonepetalactone, and matatabiether isolated from the cat- and lacewmg-attracting plant Actinidia polygama Miq. were revised to the S configurations on the basis of chemical transformations and unambiguous syntheses.

Novel synthesis of brefeldin a an application of the oxidative fragmentation of γ-hydroxyalkyl stannanes

Abstract Synthesis of Brefeldin A seco acid (13) involving new oxidative fragmentation was reported.