Sumio Shimizu

The fluoride-induced reaction of phenylthio-, methylthio- and methoxy-substituted silylmethylazoles with carbonyl compounds

Abstract Phenylthio-, methylthio- and methoxy-substituted silylmethylazoles, which act as substituted (N-azolyl)methylanion equivalents, were prepared and made to react with carbonyl compounds in the presence of fluoride anion to obtain 2-phenylthio-, 2-methylthio- and 2-methoxy-substituted 2-azolylethanols. Also examined in this study was the lithiation of 1-methylthiomethyl-1,2,4-triazole and 1-bis(methylthio)methyl-1,2,4-triazole.

Synthesis and oral anti-fungal activity of novel 1,3-bis-(azolyl)-2-arylpropan-2-ols

Synthesis of 1-alkoxy- or 1-alkylthio-1,3-bis(azolyl)-2-anylpropan-2-ols is described. The title compounds were examined for their anti-fungal activities in vitro by evaluation of broth dilution MIC values against 3 species of fungi and the inhibitory effect on the pseudomycelium formation by Candida albicans and oral efficacy in vivo against systemic candidiasis in mice. (1R∗, 2R∗)-2-(4-Chlorophenyl)-1-methoxy-1,3-bis(1,2,4-triazol-1-yl)-2-propanol exhibited strong oral anti-fungal activity. Structure—activity relationships of the compounds examined are described.

A Convenient Synthesis of 1H-1,2,4-Triazol-1-Yl-Propan-3-One Derivatives by Modified Mannich Reaction

Abstract 1H-1,2,4-Triazol-1-yl-propan-3-ones were synthesized regioselectively using a modified Mannich reaction. Reactions of enones and Mannich bases with imidazole are also described.

CONVERGENT SYNTHESIS OF S-8921, A NEW POTENT HYPOCHOLESTEROLEMIC ARYLNAPHTHALENE LIGNAN ANALOG

Abstract We established a convergent synthesis of S-8921 (1), a unique hypocholesterolemic lignan analog, in 9 steps, including concise preparations of phthalide 7 and acylpropenoate 10, and their regio- and stereocontrolled tandem anionic reactions leading to precursor 11 as a key step.

Alkoxide-Induced Reaction of 1-[(Trimethylsilyl)-Methyl]Azoles with Imines and Carbonyl Compounds

Abstract t-BuOK-induced reaction of 1-[(trimethylsilyl)methyl]-1,2,4-triazole with imines to yield (triazol-1- yl)ethylamines and (triazol-5-yl)methylamines was explored. Also, alkoxide-induced desilylation of 1-[(trimethylsilyl)methyl]azoles in the presence of carbonyl compounds was demonstrated, and (-BuOK and potassium trimethylsilanolate were found to be effective in this reaction.